TAX GUIDE PLANNING 2018 2019 - Bernard Robinson & Company

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TAX GUIDE PLANNING 2018 2019 - Bernard Robinson & Company
2018 ‑ 2019

                                 TAX
                                 PLANNING
                                GUIDE

YEAR-ROUND STRATEGIES TO MAKE THE TAX LAWS WORK FOR YOU
TAX GUIDE PLANNING 2018 2019 - Bernard Robinson & Company
Dear Clients and Friends,

No one can tell you exactly what is going to happen in the coming months with the economy,
our tax laws and your personal financial situation. However, you can be assured of this; if you
want to minimize your taxes, you must have a plan, not only to move toward your goals, but
also to know what adjustments to make as things change.

Bernard Robinson & Company has provided extensive tax services to our valued clients for
70 years. Our team of dedicated professionals continually stay abreast of existing tax laws,
proposed laws, regulations and planning strategies. With economic and legislative uncertainty
now a given, it is more important than ever to have experience on your side when reacting
quickly to changes to take advantage of new ways to save tax and protect your wealth.

To these ends, we’re pleased to present this tax planning guide. It’s designed to help you under-
stand what the current tax law situation is, where changes may occur and what steps you might
take to minimize your income or estate tax. We encourage you to look through it and note any
strategies that seem likely to benefit you. Then let us know how we can help you develop a plan
that keeps your income or estate tax liability as low as possible.

Also, don’t wait until filing time! Tax planning is a year-round activity. To get the most benefit,
you should act now.

We would like very much to talk with you about these and other ways to minimize your taxes.
Please contact us at your earliest convenience and let us know how we might be of assistance.

Best regards,

Bernard Robinson & Company Tax Leadership
TAX GUIDE PLANNING 2018 2019 - Bernard Robinson & Company
It’s a new day
for tax planning
On December 22, 2017, the most sweeping tax legislation since the Tax Reform
Act of 1986 was signed into law. The Tax Cuts and Jobs Act (TCJA) makes small
reductions to income tax rates for most individual tax brackets, including reducing
the top rate from 39.6% to 37%, and substantially reduces the income tax rate for
corporations. It also provides a large new tax deduction for owners of pass-through
entities and significantly increases exemptions for the individual alternative minimum
tax (AMT) and the estate tax.

It’s not all good news for taxpayers, however. The TCJA also eliminates or limits
many tax breaks, and much of the tax relief provided is only temporary (unless
Congress acts to make it permanent). The combined impact of these changes will
ultimately determine whether you see reduced taxes. It also will dictate which tax
strategies will make sense for you this year, such as the best way to time income
and expenses.

This guide provides an overview of the most consequential changes under the TCJA
and other key tax provisions you need to be aware of. It offers a variety of strategies
to help higher-income taxpayers minimize their taxes in the new tax environment. It
will be important to work closely with your tax advisor this year. He or she can help
you identify which changes affect you and the best strategies for maximizing the
new tax law’s benefits and minimizing any negative tax ramifications. Plus, more
tax legislation could be signed into law this year, and your tax advisor can keep you
apprised of the latest information.

Contents
YEAR-TO-DATE REV IEW ......... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2          Click here

E XECUTIV E COMPENSATION .. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 6               Click here

I NV ESTING.......................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 8   Click here

REAL ESTATE.. ...................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 12     Click here

BUSINESS OWNERSHIP . . ........ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 14          Click here

CHARITAB LE G IV ING . . .......... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 16      Click here

FAMILY & ED UCATION .......... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 18           Click here

RETIREMENT . ....................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 20     Click here

ESTATE PLANNING ............... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 22          Click here

TAX RATES .......................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 24     Click here
TAX GUIDE PLANNING 2018 2019 - Bernard Robinson & Company
How does the TCJA
                              affect your tax strategies?

                              T
                                    he Tax Cuts and Jobs Act (TCJA) reduces the rates for all individual income tax             Finally, in certain situations exercising
                                    brackets except 35% and 10%, which remain the same, and adjusts the income                  incentive stock options (ISOs) can trigger
                                    ranges each bracket covers. (See Chart 7 on page 24.) These rates apply to                  significant AMT liability. (See the AMT
                              “ordinary income,” which generally includes salary, income from self-employment                   Alert on page 7.)
                              or business activities, interest, and distributions from tax-deferred retirement accounts.
                              There are other taxes you need to keep in mind as well, such as the AMT and                       Avoiding or reducing AMT
                              employment taxes. If possible, try to control to your tax advantage the timing of your
                                                                                                                                With proper planning, you may be able
                              ordinary income as well as your deductible expenses — which might be significantly
                                                                                                                                to avoid the AMT, reduce its impact
                              reduced under the TCJA.
                                                                                                                                or even take advantage of its lower
                                                                                                                                maximum rate. To determine the right
                              AMT triggers                                  n	Accelerated depreciation adjustments
                                                                                                                                timing strategies for your situation, work
                                                                                  and related gain or loss differences          with your tax advisor to assess whether:
                              The top alternative minimum tax rate
                                                                                  when assets are sold, and
                              remains at 28%, compared to the new
                              top regular ordinary-income tax rate          n	Tax-exempt      interest on certain              You could be subject to the AMT this
                              of 37%. (See Chart 7 on page 24.)                   private-activity municipal bonds.             year. Consider accelerating income
                              But the AMT rate typically applies to a             (For an exception, see the AMT                into this year, which may allow you to
                              higher taxable income base.                         Alert on page 11.)                            benefit from the lower maximum AMT

                              Enhancement! The TCJA substantially
                                                                              CHART 1
                              increases the AMT exemptions for
                              2018–2025, which means fewer                    What itemized deductions are
                              taxpayers will have to pay the AMT.             also deductible for AMT purposes?
                              (See Chart 7 on page 24.) There are
                              now fewer differences between what’s                          Expense                 Regular tax       AMT        For more information
                              deductible for AMT purposes and regu-
                                                                                                                                                See “What’s new!” on
                              lar tax purposes, which also will reduce            State and local income tax1            ✔                      page 4.
                              AMT risk. However, AMT will remain a
                              threat for some higher-income taxpayers.                                                                          See “Home-related
                                                                                  Property tax1                          ✔                      deductions” on page 12.
                              So before timing your income and                                                                                  See “Home-related
                              expenses, determine whether you’re                  Mortgage interest                      ✔             ✔        deductions” on page 12.
                              already likely to be subject to the AMT —
                                                                                  Interest on home equity debt
                              or whether the actions you’re considering                                                                         See “Home-related
                                                                                  used to improve your principal         ✔             ✔        deductions” on page 12.
                              might trigger it. Deductions used to                residence or second residence
                              calculate regular tax that aren’t allowed
                                                                                                                                                See “Investment interest
                              under the AMT (see Chart 1) can trigger             Investment interest                    ✔             ✔
YE A R- TO- DAT E RE VI E W

                                                                                                                                                expense” on page 11.
                              AMT liability. Some income items also
                              might trigger or increase AMT liability:                                                                          See “Health-care-related
                                                                                  Medical expenses                       ✔             ✔        breaks” at right.
                              n	Long-term capital gains and qualified
                                                                                  Charitable contributions               ✔             ✔        See page 16.
                                 dividend income, even though they’re
                                 taxed at the same rate for both regular
                                                                              1
                                                                               	State and local income tax and property tax deductions in aggregate are limited to $10,000 for
                                                                                regular tax purposes ($5,000 for married couples filing separately).
                                 tax and AMT purposes,
     2
TAX GUIDE PLANNING 2018 2019 - Bernard Robinson & Company
rate. And deferring expenses you can’t
deduct for AMT purposes may allow
                                                    WHAT’S NEW!
you to preserve those deductions. If you
also defer expenses you can deduct                  Dramatic changes to personal exemptions, the
for AMT purposes, the deductions                    standard deduction and itemized deductions
may become more valuable because
of the higher maximum regular tax                   For 2017, taxpayers could
rate. Finally, carefully consider the tax           claim a personal exemption
consequences of exercising ISOs.                    of $4,050 each for them-
                                                    selves, their spouses and any
You could be subject to the AMT next                dependents. For 2018–2025,
year. Consider taking the opposite                  the Tax Cuts and Jobs Act
approach. For instance, defer income                (TCJA) suspends personal
to next year, because you’ll likely pay a           exemptions, a change that’s
relatively lower AMT rate. And prepay               expected to have minimal
expenses that will be deductible this year          effect on higher-income
but that won’t help you next year because           taxpayers. That’s because exemptions generally had been partially or fully
they’re not deductible for AMT purposes.            phased out in past tax years for higher-income individuals and, when
Also, before year end consider selling any          available, were added back for AMT purposes.
private-activity municipal bonds whose
interest could be subject to the AMT.               The TCJA also nearly doubles the standard deductions for 2018 to $12,000
                                                    for singles and separate filers, $18,000 for heads of households, and $24,000
If you pay AMT in one year on deferral              for joint filers. (These amounts will be indexed for inflation through 2025. After
items, such as depreciation adjustments,            that, they’re scheduled to drop back to the amounts under pre-TCJA law.)
passive activity adjustments or the tax
preference on ISO exercises, you may be             Taxpayers can choose to either itemize certain deductions or take the
entitled to a credit in a subsequent year.          standard deduction based on their filing status. With the much higher
In effect, this factors in timing differences       standard deduction, fewer taxpayers will itemize — but most higher-income
that reverse in later years.                        taxpayers will still benefit from itemizing, unless they don’t donate much to
                                                    charity or have a mortgage. However, be aware that your itemized deductions
                                                    will likely be significantly lower than in the past because of other TCJA
Timing income and expenses
                                                    changes. See “What’s new!” on page 4.
Smart timing of income and expenses can
reduce your tax liability, and poor timing
can unnecessarily increase it. When you          Whatever the reason behind your              Eligible expenses may include health
don’t expect to be subject to the AMT in         desire to time income and expenses,          insurance premiums, long-term-care
the current year or the next year, deferring     you may be able to control the timing        insurance premiums (limits apply),
income to the next year and accelerating         of these income items:                       medical and dental services, and pre-
deductible expenses into the current year                                                     scription drugs. Mileage driven for health
                                                 n	Bonuses,                                  care purposes also can be deducted —
may be a good idea. Why? Because it will
defer tax, which usually is beneficial.          n	Consulting   or other self-employment     at 18 cents per mile for 2018.
                                                   income,
But when you expect to be in a higher                                                         When a deduction is subject to a floor,
                                                 n	U.S.   Treasury bill income, and
tax bracket next year — or you expect                                                         “bunching” expenses into one year that
                                                 n	Retirement plan distributions, to         normally would be spread over two years
tax rates to rise — the opposite approach
                                                   the extent they won’t be subject to        can save tax, especially when the floor is
may be beneficial: Accelerating income
                                                   early-withdrawal penalties and aren’t      scheduled to change. So consider bunch-
will allow more income to be taxed at
                                                   required. (See page 21.)                   ing elective medical procedures (and
your current year’s lower rate. And defer-
ring expenses will make the deductions                                                        any other services and purchases whose
                                                 Some expenses with potentially
more valuable, because deductions save                                                        timing you can control without negatively
                                                 controllable timing are mortgage
more tax when you’re subject to a higher                                                      affecting your or your family’s health) into
                                                 interest, investment interest expense
tax rate.                                                                                     2018 to take advantage of the 7.5% floor.
                                                 and charitable contributions.

The TCJA makes timing income and                                                              If one spouse has high medical
deductions more challenging this year,           Health-care-related breaks                   expenses and a relatively lower AGI,
because some strategies that taxpayers           Enhancement! Under the TCJA, if              filing separately may allow that spouse
have implemented in the past may                 2018 medical expenses not paid via a         to exceed the AGI floor and deduct
                                                                                              some medical expenses that wouldn’t
                                                                                                                                             YE AR -TO- DAT E RE VI E W

no longer make sense. For example,               tax-advantaged account (see page 4)
property tax used to be a popular                or reimbursable by insurance exceed          be deductible if the couple filed jointly.
expense to time, but with the new limit          7.5% of your adjusted gross income
                                                                                              AMT ALERT! Because the AMT exemp-
on the state and local tax deduction             (AGI), you can deduct the excess
                                                                                              tion for separate returns is considerably
(see “What’s new!” on page 4), property          amount. This “floor” had been 10%,
                                                                                              lower than the exemption for joint
tax timing will likely provide little, if any,   and it’s scheduled to return to 10%
                                                                                              returns, filing separately to exceed the
benefit for higher-income taxpayers.             beginning in 2019.
                                                                                              floor could trigger the AMT.
                                                                                                                                                3
TAX GUIDE PLANNING 2018 2019 - Bernard Robinson & Company
Expenses that are reimbursable by            $2,650 in 2018. The plan pays or           Self-employment taxes
                              insurance or paid through a tax-             reimburses you for qualified medical       If you’re self-employed, you pay both
                              advantaged account such as the               expenses. What you don’t use by the        the employee and employer portions
                              following aren’t deductible:                 plan year’s end, you generally lose —      of employment taxes on your self-
                                                                           though your plan might allow you to        employment income. The employer
                              HSA. If you’re covered by a qualified        roll over up to $500 to the next year.     portion (6.2% for Social Security tax and
                              high deductible health plan, you can         Or it might give you a 2½-month grace      1.45% for Medicare tax) is deductible
                              contribute pretax income to an employer-     period to incur expenses to use up         above the line.
                              sponsored Health Savings Account — or        the previous year’s contribution. If you
                              make deductible contributions to an HSA      have an HSA, your FSA is limited to        As a self-employed taxpayer, you may
                              you set up yourself — up to $3,450 for       funding certain “permitted” expenses.      benefit from other above-the-line deduc-
                              self-only coverage and $6,900 for family
                                                                                                                      tions as well. You can deduct 100%
                              coverage for 2018. Plus, if you’re age 55
                                                                           Employment taxes                           of health insurance costs for yourself,
                              or older, you may contribute an additional
                                                                           In addition to income tax, you must        your spouse and your dependents, up
                              $1,000. HSAs can bear interest or be
                                                                           pay Social Security and Medicare           to your net self-employment income.
                              invested, growing tax-deferred similar to
                                                                           taxes on earned income, such as            You also can deduct contributions
                              an IRA. Withdrawals for qualified medical
                                                                           salary and bonuses. The 12.4%              to a retirement plan and, if you’re
                              expenses are tax-free, and you can carry
                                                                           Social Security tax applies only up        eligible, an HSA for yourself. And you
                              over a balance from year to year.
                                                                           to the Social Security wage base of        might be able to deduct home office
                                                                           $128,400 for 2018. All earned income       expenses. (See page 12.) Above-the-line
                              FSA. You can redirect pretax income
                                                                           is subject to the 2.9% Medicare tax.       deductions are particularly valuable
                              to an employer-sponsored Flexible
                                                                           Both taxes are split equally between       because they reduce your AGI and,
                              Spending Account up to an employer-
                                                                           the employee and the employer.             depending on the specific deduction,
                              determined limit — not to exceed
                                                                                                                      your modified AGI (MAGI), which are
                                                                                                                      the triggers for certain additional taxes
                                                                                                                      and the phaseouts of many tax breaks.
                                 WHAT’S NEW!

                                 Individual deductions affected by the TCJA                                           Additional 0.9% Medicare tax
                                                                                                                      Another employment tax that higher-
                                                  In addition to the deduction changes impacting many
                                                                                                                      income taxpayers must be aware of is the
                                                  home-related expenses (see page 12), charitable donations
                                                                                                                      additional 0.9% Medicare tax. It applies
                                                  (see page 16) and medical expenses (see page 3), the
                                                                                                                      to FICA wages and net self-employment
                                                  TCJA limits or eliminates other deductions that are valuable
                                                                                                                      income exceeding $200,000 per year
                                                  to many individual taxpayers:
                                                                                                                      ($250,000 if married filing jointly and
                                                                                                                      $125,000 if married filing separately).
                                 State and local tax. For 2018–2025, your entire itemized deduction for
                                 state and local taxes — including property tax (see page 12) and either
                                                                                                                      If your wages or self-employment
                                 income or sales tax — is limited to $10,000 ($5,000 if you’re married filing
                                                                                                                      income varies significantly from year
                                 separately). This will have a significant impact on higher-income taxpayers
                                                                                                                      to year or you’re nearing the threshold
                                 with large state and local income tax and/or property tax bills.
                                                                                                                      for triggering the additional Medicare
                                                                                                                      tax, income timing strategies may help
                                 Miscellaneous itemized deductions subject to the 2% floor. This deduction
                                                                                                                      you avoid or minimize it. For example,
                                 for expenses such as certain professional fees, investment expenses and
                                                                                                                      if you’re an employee, perhaps you
                                 unreimbursed employee business expenses is suspended for 2018–2025.
                                                                                                                      can time when you receive a bonus
                                 If you’re an employee and work from home, this includes the home office
                                                                                                                      or exercise stock options. If you’re
                                 deduction. (If you’re self-employed, you may still be able to deduct home
                                                                                                                      self-employed, you may have flexibility
                                 office expenses. See page 12.)
                                                                                                                      on when you purchase new equipment
                                 Personal casualty and theft loss deduction. For 2018–2025, this itemized             or invoice customers. If you’re an
                                 deduction is suspended except if the loss was due to an event officially             S corporation shareholder-employee,
                                 declared a disaster by the President.                                                you might save tax by adjusting how
                                                                                                                      much you receive as salary vs. distribu-
                                 Moving expenses. This above-the-line deduction for work-related moving               tions. (See “Owner-employees” at right.)
                                 expenses is suspended for 2018–2025, except for active-duty members of
                                 the Armed Forces (and their spouses or dependents) who move because of a             Also consider the withholding rules.
                                 military order that calls for a permanent change of station. An above-the-line       Employers must withhold the addi-
                                 deduction is one you can take even if you don’t itemize; it’s subtracted from        tional tax beginning in the pay period
YE A R- TO- DAT E RE VI E W

                                 your income in determining your adjusted gross income (AGI).                         when wages exceed $200,000 for the
                                                                                                                      calendar year — without regard to an
                                 But it’s not all bad news for tax deductions. Under pre-TCJA law, if your AGI        employee’s filing status or income from
                                 exceeded the applicable threshold, certain itemized deductions were reduced          other sources. So your employer might
                                 by 3% of the AGI amount over the threshold (not to exceed 80% of otherwise           withhold the tax even if you aren’t liable
                                 allowable deductions). For 2018–2025, the TCJA suspends this reduction.              for it — or it might not withhold the tax
                                                                                                                      even though you are liable for it.
     4
TAX GUIDE PLANNING 2018 2019 - Bernard Robinson & Company
Estimated payments
   WHAT’S NEW!                                                                          and withholding
                                                                                        You can be subject to penalties if you
   Updated tables could cause underwithholding
                                                                                        don’t pay enough tax during the year
                                    To reflect changes under the TCJA — such            through estimated tax payments and
                                    as the increase in the standard deduction,          withholding. Here are some strategies
                                    suspension of personal exemptions and               to help avoid underpayment penalties:
                                    changes in tax rates and brackets — the
                                    IRS updated the tables that indicate how            Know the minimum payment rules. For
                                    much employers should withhold from their           you to avoid penalties, your estimated
                                    employees’ paychecks for federal income             payments and withholding must equal
                                    taxes, generally reducing the amount                at least 90% of your tax liability for 2018
                                    withheld. The new tables might cause                or 110% of your 2017 tax (100% if your
                                    some taxpayers, such as those who itemize           2017 AGI was $150,000 or less or, if
                                    deductions or are in a two-income house-            married filing separately, $75,000 or
                                    hold, to not have enough withheld to pay            less). Warning: You may be at a greater
                                    their ultimate tax liabilities under the TCJA.      risk for underwithholding this year. See
                                                                                        “What’s new!” at left.
   An IRS calculator can help you more accurately estimate how much should
   be withheld. (Go to IRS.gov and search “withholding.”) You may find that             Use the annualized income installment
   you need to increase your withholding by filling out a new Form W-4 and              method. This method often benefits
   submitting it to your employer. You can modify your withholding at any time          taxpayers who have large variability
   during the year, or even multiple times within a year.                               in income from month to month due
                                                                                        to bonuses, investment gains and
                                                                                        losses, or seasonal income (at least if
If you don’t owe the tax but your           company income, because distributions       it’s skewed toward the end of the year).
employer is withholding it, you can         generally aren’t taxed at the corporate     Annualizing computes the tax due based
claim a credit on your 2018 income tax      level or subject to the 0.9% Medicare       on income, gains, losses and deductions
return. If you do owe the tax but your      tax or 3.8% NIIT.                           through each estimated tax period.
employer isn’t withholding it, consider
filing a W-4 form to request additional     C corporations. Only income you receive     Estimate your tax liability and increase
income tax withholding, which can be        as salary is subject to employment taxes    withholding. If you determine you’ve
used to cover the shortfall and avoid       and, if applicable, the 0.9% Medicare       underpaid, consider having the tax
interest and penalties. Or you can          tax. Nonetheless, you may prefer to         shortfall withheld from your salary or year
make estimated tax payments.                take more income as salary (which is        end bonus by Dec. 31. Because with-
                                            deductible at the corporate level) as       holding is considered to have been paid
                                            opposed to dividends (which aren’t          ratably throughout the year, this is often
Owner-employees
                                            deductible at the corporate level yet are   a better strategy than making up the
There are special considerations if         still taxed at the shareholder level and    difference with an increased quarterly
you’re a business owner who also            could be subject to the 3.8% NIIT) if the   tax payment, which may still leave you
works in the business, depending on         overall tax paid by both the corporation    exposed to penalties for earlier quarters.
its structure:                              and you would be less.
                                                                                        Warning: You can incur interest and
Partnerships and limited liability          Warning: The IRS is cracking down on        penalties if you’re subject to the additional
companies. Generally, all trade or          misclassification of corporate payments     0.9% Medicare tax and it isn’t withheld
business income that flows through to       to shareholder-employees, so tread          from your pay and you don’t make
you for income tax purposes is subject      carefully.                                  sufficient estimated tax payments. ❖
to self-employment taxes — even if
the income isn’t distributed to you. But
such income may not be subject to
self-employment taxes if you’re a limited
partner or the LLC member equivalent.
Check with your tax advisor on whether
the additional 0.9% Medicare tax on
earned income or the 3.8% NIIT (see
page 8) will apply.
                                                                                                                                        YE AR -TO- DAT E RE VI E W

S corporations. Only income you
receive as salary is subject to employ-
ment taxes and, if applicable, the 0.9%
Medicare tax. To reduce these taxes,
you may want to keep your salary
relatively — but not unreasonably —
low and increase your distributions of
                                                                                                                                           5
TAX GUIDE PLANNING 2018 2019 - Bernard Robinson & Company
Smart tax planning for your executive
                                      compensation package is crucial

                                      I
                                        f you’re an executive or other key employee, you might receive stock-based                But they do offer a limited ability to defer
                                        compensation, such as restricted stock, restricted stock units (RSUs) or stock            income taxes: Unlike restricted stock,
                                        options (either incentive or nonqualified), or nonqualified deferred compensation         which becomes taxable immediately
                                      (NQDC). The tax consequences of these types of compensation can be complex —                upon vesting, RSUs aren’t taxable until
                                      subject to ordinary income, capital gains, employment and other taxes. So smart             the employee actually receives the
                                      tax planning is crucial.                                                                    stock. So rather than having the stock
                                                                                                                                  delivered immediately upon vesting,
                                      Restricted stock                             There are some potential disadvan-             you may be able to arrange with your
                                                                                   tages of a Sec. 83(b) election,                employer to delay delivery.
                                      Restricted stock is stock your employer
                                      grants to you subject to a substantial       however. First, prepaying tax in the
                                                                                   current year could push you into a             Such a delay will defer income tax
                                      risk of forfeiture. Income recognition                                                      and may allow you to reduce or
                                      is normally deferred until the stock         higher income tax bracket and trigger
                                                                                   or increase your exposure to the               avoid exposure to the additional 0.9%
                                      is no longer subject to that risk (that                                                     Medicare tax (because the RSUs are
                                      is, it’s vested) or you sell it. When the    additional 0.9% Medicare tax. But
                                                                                   if your company is in the earlier              treated as FICA income). However, any
                                      restriction lapses, you pay taxes on the                                                    income deferral must satisfy the strict
                                      stock’s fair market value (FMV) at your      stages of development, the income
                                                                                   recognized may be relatively small.            requirements of Internal Revenue Code
                                      ordinary-income rate. (The FMV will be                                                      Section 409A. Also keep in mind that it
                                      considered FICA income, so it could                                                         might be better to recognize income now
                                                                                   Second, any taxes you pay because of
                                      trigger or increase your exposure to                                                        because of the currently low tax rates.
                                                                                   the election can’t be refunded if you
                                      the additional 0.9% Medicare tax. See
                                                                                   eventually forfeit the stock or sell it
                                      page 4.)
                                                                                   at a decreased value. However, you’d           Incentive stock options
                                      But you can instead make a Section 83(b)     have a capital loss in those situations.       ISOs allow you to buy company stock in
                                      election to recognize ordinary income                                                       the future (but before a set expiration
                                                                                   Third, when you sell the shares, any
                                      when you receive the stock. This election,                                                  date) at a fixed price equal to or greater
                                                                                   gain will be included in net investment
                                      which you must make within 30 days                                                          than the stock’s FMV at the date of
                                                                                   income and could trigger or increase
                                      after receiving the stock, allows you                                                       the grant. Thus, ISOs don’t provide a
                                                                                   your liability for the 3.8% NIIT. (See
                                      to convert potential future appreciation                                                    benefit until the stock appreciates in
                                                                                   page 8.)
                                      from ordinary income to long-term capital                                                   value. If it does, you can buy shares at
                                      gains income and defer it until the stock    Work with your tax advisor to map              a price below what they’re then trading
                                      is sold.                                     out whether the Sec. 83(b) election is         for, provided you’re eligible to exercise
                                                                                   appropriate for you in each situation.         the options.
                                      The election can be beneficial if the
                                      income at the grant date is negligible                                                      ISOs receive tax-favored treatment
E X E C UT I VE C O M PE NS AT I ON

                                      or the stock is likely to appreciate
                                                                                   RSUs                                           but must comply with many rules.
                                      significantly before income would            RSUs are contractual rights to receive         Here are the key tax consequences:
                                      otherwise be recognized. And with            stock, or its cash value, after the award
                                      ordinary-income rates now especially         has vested. Unlike restricted stock, RSUs      n	You owe no tax when ISOs are
                                      low under the Tax Cuts and Jobs Act          aren’t eligible for the Sec. 83(b) election.      granted.
                                      (TCJA), it might be a good time to           So there’s no opportunity to convert           n	Youowe no regular income tax
                                      recognize income.                            ordinary income into capital gains.               when you exercise the ISOs.

       6
TAX GUIDE PLANNING 2018 2019 - Bernard Robinson & Company
n	Ifyou sell the stock after holding the
   shares at least one year from the
                                               WHAT’S NEW!
   exercise date and two years from the
   grant date, you pay tax on the sale at      The TCJA offers new, but limited, tax deferral opportunity
   your long-term capital gains rate. You
                                               The TCJA has created a
   also may owe the NIIT. (See page 8.)
                                               new provision that allows
n	Ifyou sell the stock before long-term       for the deferral of tax on
   capital gains treatment applies, a          stock-based compensation
   “disqualifying disposition” occurs and      in certain circumstances.
   any gain is taxed as compensation at        Generally, it gives taxpayers
   ordinary-income rates. (Disqualified        the opportunity to match
   dispositions aren’t, however, subject       the taxation of restricted
   to FICA and Medicare tax, including         stock and stock options
   the additional 0.9% Medicare tax.)          with the timing of the sale
                                               of the stock. It’s intended
AMT ALERT! If you don’t sell the
                                               for situations in which there
stock in the year of exercise, a tax
                                               is no ready market for the
“preference” item is created for the
                                               sale of the stock.
difference between the stock’s FMV
and the exercise price (the “bargain           The availability of the deferral opportunity is limited, however. It generally
element”) that can trigger the AMT.            will apply only if at least 80% of full-time employees are covered by the
A future AMT credit, however, should           stock-based compensation plan.
mitigate this AMT hit. Plus, you may
now be at lower AMT risk because
of the higher AMT exemption and
                                            On the negative side, exercising early       NQDC plans
exemption phaseout range under
                                            accelerates the need for funds to
the TCJA. (See Chart 7 on page 24.)                                                      These plans pay executives in the
                                            buy the stock, exposes you to a loss
Consult your tax advisor because the                                                     future for services to be currently
                                            if the shares’ value drops below
rules are complex.                                                                       performed. They differ from qualified
                                            your exercise cost, and may create
                                                                                         plans, such as 401(k)s, in several
                                            a tax cost if the preference item
If you’ve received ISOs, plan carefully                                                  ways. For example, unlike 401(k)
                                            from the exercise generates an
when to exercise them and whether                                                        plans, NQDC plans can favor highly
                                            AMT liability.
to immediately sell shares received                                                      compensated employees, but plan
from an exercise or hold them. Waiting                                                   funding isn’t protected from the
                                            The timing of ISO exercises also could
to exercise ISOs until just before the                                                   employer’s creditors. (For more on
                                            positively or negatively affect your
expiration date (when the stock value                                                    401(k)s, see page 20.)
                                            liability for the higher ordinary-income
may be the highest, assuming the
                                            tax rates, the 20% long-term capital
stock is appreciating) and holding on to                                                 Some major changes to the taxation
                                            gains rate and the NIIT.
the stock long enough to garner long-                                                    of NQDC that had been included
term capital gains treatment often is                                                    in original versions of the TCJA
                                            With your tax advisor, evaluate the risks
beneficial. But there’s also market risk                                                 would have negatively impacted
                                            and crunch the numbers to determine
to consider. Plus, acting earlier can be                                                 such compensation. Fortunately,
                                            the best strategy for you.
advantageous in several situations:                                                      those changes didn’t make it into
                                                                                         the final version that was signed
n	Exercise early to start the holding
                                            Nonqualified stock options                   into law.
   period so you can sell and receive       The tax treatment of NQSOs is
   long-term capital gains treatment        different from the tax treatment of          One important NQDC tax issue is that
   sooner.                                  ISOs: NQSOs create compensation              employment taxes (see page 4) are
                                            income (taxed at ordinary-income             generally due once services have been
n	Exercise  when the bargain element
                                            rates) on the bargain element when           performed and there’s no longer a
   is small or when the market price is
                                            exercised (regardless of whether the         substantial risk of forfeiture — even
   close to bottoming out to reduce or
                                            stock is held or sold immediately),          though compensation may not be
   eliminate AMT liability.
                                            but they don’t create an AMT                 paid or recognized for income tax
n	Exercise annually so you can buy         preference item.                             purposes until much later. So your
   only the number of shares that will                                                   employer may withhold your portion
                                                                                                                                 E X E C U TI VE C O M P E NSATI O N

   achieve a breakeven point between        You may need to make estimated tax           of the employment taxes from your
   the AMT and regular tax and thereby      payments or increase withholding to          salary or ask you to write a check
   incur no additional tax.                 fully cover the tax on the exercise.         for the liability. Or it may pay your
n	Sell in a disqualifying disposition      Keep in mind that an exercise could          portion, in which case you’ll have
   and pay the higher ordinary-income       trigger or increase exposure to top tax      additional taxable income. Warning:
   rate to avoid the AMT on potentially     rates, the additional 0.9% Medicare          The additional 0.9% Medicare tax
   disappearing appreciation.               tax and the NIIT.                            could also apply. ❖

                                                                                                                                      7
TAX GUIDE PLANNING 2018 2019 - Bernard Robinson & Company
Keep taxes from eroding
                 your investment returns

                 T
                       ax treatment of your investments varies dramatically based on factors such      New! Because of TCJA-related changes
                       as type of investment, type of income it produces, how long you’ve held it      to the brackets, beginning in 2018 the
                       and whether any special limitations or breaks apply. And while the Tax Cuts     top long-term gains rate of 20% kicks
                 and Jobs Act (TCJA) didn’t change the long-term capital gains rates, its changes to   in before the top ordinary-income rate
                 ordinary-income tax rates and tax brackets will have an impact on the tax you pay     does. (See Chart 2 on page 10 and
                 on investments. Consult with your tax advisor about developing strategies aimed at    Chart 7 on page 24.)
                 minimizing tax, keeping in mind that taxes, of course, should never be the primary
                 driver of your investment decisions.                                                  Holding on to an investment until you’ve
                                                                                                       owned it more than one year may help
                                                                                                       substantially cut tax on any gain. Keeping
                 3.8% NIIT                                  Capital gains tax and timing
                                                                                                       it even longer can also make tax sense.
                 Taxpayers with modified adjusted           Although time, not timing, is generally
                 gross income (MAGI) over $200,000          the key to long-term investment            Remember: Appreciation on investments
                 per year ($250,000 if married filing       success, timing can have a dramatic        isn’t taxed until the investments are sold,
                 jointly and $125,000 if married filing     impact on the tax consequences of          deferring tax and perhaps allowing you
                 separately) may owe the NIIT on top        investment activities. Your long-term      to time the sale to your tax advantage —
                 of whatever other tax they owe on          capital gains rate can be as much          such as in a year when you have capital
                 their investment income. The NIIT          as 20 percentage points lower              losses to absorb the capital gain. Or, if
                 equals 3.8% of the lesser of your net      than your ordinary-income tax rate,        you’ve cashed in some big gains during
                 investment income or the amount            even with the reductions to most           the year and want to reduce your 2018
                 by which your MAGI exceeds the             ordinary-income rates under the            tax liability, before year end look for
                 applicable threshold.                      TCJA. The long-term capital gains          unrealized losses in your portfolio and
                                                            rate applies to investments held for       consider selling them to offset your gains.
                 Net investment income can include          more than 12 months. The applicable        Both long- and short-term gains and
                 capital gains, dividends, interest and     rate depends on your income level          losses can offset one another.
                 other investment-related income (but not   and the type of asset you’ve sold. (See
                 business income or self-rental income      Chart 2 on page 10.)                       AMT ALERT! Substantial net long-term
                 from an active trade or business). The                                                capital gains can trigger the AMT.
                 rules are somewhat complex, so consult
                 your tax advisor for more information.

                 Many of the strategies that can help
                 you save or defer income tax on your
                 investments can also help you avoid
                 or defer NIIT liability. And because
                 the threshold for the NIIT is based
                 on MAGI, strategies that reduce your
                 MAGI — such as making retirement
                 plan contributions (see page 20) —
                 could also help you avoid or reduce
I NV E ST I NG

                 NIIT liability.

  8
Wash sale rule
                                                  Case Study I
If you want to achieve a tax loss with
minimal change in your portfolio’s asset          How to qualify for the 0% capital gains rate
allocation, keep in mind the wash sale
rule. It prevents you from taking a loss on                                                 Faced with a long-term capital gains
a security if you buy a substantially iden-                                                 tax rate of 23.8% (20% for the top
tical security (or an option to buy such a                                                  tax bracket, plus the 3.8% NIIT),
security) within 30 days before or after                                                    Miguel and Pilar decide to give some
you sell the security that created the loss.                                                appreciated stock to their adult
You can then recognize the loss only                                                        daughter Gabby. Just out of college
when you sell the replacement security.                                                     and making only enough from her
                                                                                            entry-level job to leave her with
Fortunately, there are ways to avoid trig-                                                  $25,000 in taxable income, Gabby
gering the wash sale rule and still achieve                                                 falls into the 12% ordinary-income
your goals. For example, you can:                                                           tax bracket and the 0% long-term
                                                                                            capital gains bracket.
n	Sell the security and immediately
   buy securities of a different company          However, the 0% rate applies only to the extent that capital gains “fill
   in the same industry or shares in a            up” the gap between Gabby’s taxable income and the top end of the 0%
   mutual fund that holds securities              bracket. For 2018, the 0% bracket for singles tops out at $38,600 (just
   much like the ones you sold,                   $100 less than the top of the 12% ordinary-income bracket). So if Gabby
n	Sellthe security and wait 31 days to           sells the stock her parents transferred to her and her gains are $13,600,
   repurchase the same security, or               the entire amount will qualify for the 0% rate. The sale will be tax-free
                                                  vs. the $3,237 Miguel and Pilar would have owed had they sold the
n	Before   selling the security, purchase
                                                  stock themselves.
   additional shares of that security
   equal to the number you want to
   sell at a loss, and then wait 31 days       Finally, remember that capital gains          And if you bought the same security
   to sell the original portion.               distributions from mutual funds can           at different times and prices and want
                                               also absorb capital losses.                   to sell high-tax-basis shares to reduce
Alternatively, you can do a bond swap,
                                                                                             gain or increase a loss to offset other
where you sell a bond, take a loss and
                                               0% rate                                       gains, be sure to specifically identify
then immediately buy another bond
                                                                                             which block of shares is being sold.
of similar quality and duration from a         The 0% rate generally applies to
different issuer. Generally, the wash sale     long-term gain that would be taxed at
rule doesn’t apply because the bonds           10% or 12%, based on the taxpayer’s           Mutual funds
aren’t considered substantially identical.     ordinary-income rate. However, a very         Investing in mutual funds is an easy
Thus, you can achieve a tax loss with          small portion of income in the top of         way to diversify your portfolio. But
virtually no change in economic position.      the 12% brackets won’t be eligible for        beware of the tax pitfalls. First,
                                               the 0% rate.                                  mutual funds with high turnover
Warning: You can’t avoid the wash                                                            rates can create income that’s taxed
sale rule by selling stock at a loss in        If you have adult children in the 10% or      at ordinary-income rates. Choosing
a taxable account and purchasing               12% tax bracket, consider transferring        funds that provide primarily long-term
the same stock within 30 days in a             appreciated assets to them so they can        gains can save you more tax dollars
tax-advantaged retirement account.             sell the assets and enjoy the 0% rate.        because of the lower long-term rates.
                                               (See Case Study I.)
Loss carryovers                                                                              Second, earnings on mutual funds are
                                               Warning: If the child will be under           typically reinvested, and unless you or
If net losses exceed net gains, you can        age 24 on Dec. 31, first make sure he         your investment advisor increases your
deduct only $3,000 ($1,500 if married          or she won’t be subject to the “kiddie        basis accordingly, you may report more
filing separately) of the net losses per       tax.” (See page 18.) Also consider any        gain than required when you sell the
year against other income (such as             gift tax consequences. (See page 22.)         fund. Brokerage firms are required to
wages, self-employment and business
                                                                                             track (and report to the IRS) your cost
income, dividends and interest).
                                               Paying attention to details                   basis in mutual funds acquired during
You can carry forward excess losses            If you don’t pay attention to the details,    the tax year.
until death. Loss carryovers can be a          the tax consequences of a sale may
                                                                                             Third, buying equity mutual fund
powerful tax-saving tool in future years       be different from what you expect.
                                                                                             shares late in the year can be costly
if you have a large investment portfolio,      For example, the trade date, not the
                                                                                             tax-wise. Such funds often declare a
real estate holdings or a closely held         settlement date, of publicly traded
                                                                                             large capital gains distribution at year
business that might generate substantial       securities determines the year in
                                                                                             end, which is a taxable event. If you
                                                                                                                                        I NV E ST I NG

future capital gains.                          which you recognize the gain or loss.

                                                                                                                                          9
own the shares on the distribution’s                proceeds, you can defer the tax on your            Keep in mind that all three of these
                 record date, you’ll be taxed on the full            gain until you dispose of the new stock.           tax benefits are subject to additional
                 distribution amount even if it includes             The rolled-over gain reduces your basis            requirements and limits. Consult your
                 significant gains realized by the fund              in the new stock. For determining                  tax and financial advisors to be sure
                 before you owned the shares. And                    long-term capital gains treatment, the             an investment in small business stock
                 you’ll pay tax on those gains in the                new stock’s holding period includes the            is right for you.
                 current year — even if you reinvest                 holding period of the stock you sold. To
                 the distribution.                                   be a QSB, a business must be engaged               Passive activities
                                                                     in an active trade or business and must
                                                                                                                        If you’ve invested in a trade or business
                 Small business stock                                not have assets that exceed $50 million,
                                                                                                                        in which you don’t materially participate
                                                                     among other requirements.
                 By purchasing stock in certain small                                                                   and where income or loss flows through
                 businesses, you can diversify your                  Exclusion of gain. Generally, taxpayers            to your tax return, remember the passive
                 portfolio. You also may enjoy preferential          selling QSB stock are allowed to exclude           activity rules. Why? Passive activity
                 tax treatment:                                      up to 50% of their gain if they’ve held            income may be subject to the 3.8% NIIT,
                                                                     the stock for more than five years. But,           and passive activity losses generally are
                 Conversion of capital loss to ordinary                                                                 deductible only against income from
                                                                     depending on the acquisition date, the
                 loss. If you sell qualifying Section 1244                                                              other passive activities. You can carry
                                                                     exclusion may be greater: The exclusion
                 small business stock at a loss, you                                                                    forward disallowed losses to the following
                                                                     is 75% for stock acquired after Feb. 17,
                 can treat up to $50,000 ($100,000,                                                                     year, subject to the same limits.
                                                                     2009, and before Sept. 28, 2010, and
                 if married filing jointly) as an ordinary,
                                                                     100% for stock acquired on or after
                 rather than a capital, loss — regardless                                                               To avoid passive activity treatment,
                                                                     Sept. 28, 2010.
                 of your holding period. This means you                                                                 you must “materially participate” in
                 can use it to offset ordinary income,               The taxable portion of any QSB gain                the activity, which typically means
                 reducing your tax by as much as 37%                 will be subject to the lesser of your              you must participate in the trade or
                 of this portion of the loss. Sec. 1244              ordinary-income rate or 28%, rather                business more than 500 hours during
                 applies only if total capital invested isn’t        than the normal long-term gains rate.              the year or demonstrate that your
                 more than $1 million.                               (See Chart 2.) Thus, if the 28% rate               involvement constitutes substantially
                                                                     and the 50% exclusion apply, the                   all of the participation in the activity.
                 Tax-free gain rollovers. If within 60 days                                                             (Special rules apply to real estate; see
                                                                     effective rate on the QSB gain will be
                 of selling qualified small business (QSB)                                                              page 13.) To help ensure your hours
                                                                     14% (28% × 50%).
                 stock you buy other QSB stock with the                                                                 claim will be able to withstand IRS
                                                                                                                        scrutiny, carefully track and document
                  CHART 2                                                                                               your time. Contemporaneous record-
                                                                                                                        keeping is better than records that
                  What’s the maximum 2018 capital gains tax rate?
                                                                                                                        are created after the fact.
                                                Type of gain                                        Rate1
                                                                                                                        If you don’t pass the material partici-
                                                                                           Taxpayer’s ordinary-         pation test, consider:
                       Short-term (assets held 12 months or less)
                                                                                             income tax rate
                                                                                                                        Increasing your involvement. If you
                       Long-term (assets held more than 12 months)                                  15%
                                                                                                                        can exceed 500 hours, the activity
                       Some key exceptions                                                                              no longer will be subject to passive
                       Long-term gain of certain higher-income taxpayers                            20%2                activity rules.

                       Most long-term gain that would be taxed at 10% or 12%                                            Grouping activities. You may be able
                                                                                                     0%
                       based on the taxpayer’s ordinary-income rate                                                     to group certain activities together
                       Long-term gain on collectibles, such as artwork and antiques                 28%                 to be treated as one activity for tax
                                                                                                                        purposes and exceed the 500-hour
                       Long-term gain attributable to certain recapture of prior
                                                                                                    25%                 threshold. But the rules are complex,
                       depreciation on real property
                                                                                                                        and there are potential downsides
                       Gain on qualified small business (QSB) stock held more                                           to consider.
                       than 5 years
                        n   	Acquired on or before Feb. 17, 2009                                   14%3                Looking at other activities. If you
                                                                                                                        have passive losses, one option is
                        n	Acquired after Feb. 17, 2009, and before Sept. 28, 2010                   7%4
                                                                                                                        to limit your participation in another
                        n   	Acquired on or after Sept. 28, 2010                                    0%                 activity that’s generating income, so
                                                                                                                        that you don’t meet the 500-hour
                   	In addition, the 3.8% NIIT applies to net investment income to the extent that modified adjusted
                   1

                    gross income (MAGI) exceeds $200,000 (singles and heads of households), $250,000 (married           test. Another is to invest in another
                    filing jointly) or $125,000 (married filing separately).                                            income-producing trade or business
                   	The 20% rate applies to taxpayers with taxable income exceeding $425,800 (singles), $452,400
                   2
                                                                                                                        that will be passive to you. Under
                    (heads of households), $479,000 (joint filers) or $239,500 (separate filers).
I NV E ST I NG

                                                                                                                        both strategies, you’ll have passive
                   	Effective rate based on a 50% exclusion from a 28% rate.
                   3
                                                                                                                        income that can absorb some or all
                   	Effective rate based on a 75% exclusion from a 28% rate.
                   4
                                                                                                                        of your passive losses.

10
Disposing of the activity. This generally
allows you to deduct all passive losses —         Case Study II
including any loss on disposition (subject
                                                  Tax-exempt or taxable bonds? It’s a question of yield
to basis and capital loss limitations). But,
again, the rules are complex.                                                                      Working with her financial
                                                                                                   advisor, Cheryl decides she
New! Even if you do pass the material
                                                                                                   needs more bonds in her
participation test, be aware that your loss
                                                                                                   investment portfolio. She’s
deduction might still be limited under the
                                                                                                   in the 37% bracket, so she’s
TCJA’s new rules for deducting business
                                                                                                   leaning toward municipal
losses. See page 14.
                                                                                                   bonds. After all, municipal
                                                                                                   bond interest will be tax-free
Income investments                                                                                 on Cheryl’s federal return.
Qualified dividends are taxed at the
favorable long-term capital gains                                                                 But the fact that an invest-
tax rate rather than at your higher                                                               ment is tax-exempt doesn’t
ordinary-income tax rate.                                                                         necessarily make it a better
                                                                                                  choice than a comparable
Interest income, however, generally                                                               taxable investment. Municipal
is taxed at ordinary-income rates. So                                                             bonds typically offer lower
stocks that pay qualified dividends may           yields than comparable corporate bonds. To make a fair comparison, Cheryl
be more attractive tax-wise than other            needs to calculate the tax-equivalent yield — which incorporates tax savings
income investments, such as CDs and               into the municipal bond’s yield — using this formula:
taxable bonds. But there are exceptions.
                                                  Tax-equivalent yield = actual yield / (1 – Cheryl’s marginal tax rate).
Some dividends, for example, are subject
to ordinary-income rates. These include           For example, Cheryl considers a municipal bond with a 4.00% yield
certain dividends from:                           and a comparable corporate bond that offers a 6.25% yield. Because
                                                  she’s in the 37% tax bracket, the municipal bond’s tax-equivalent yield is
n	Real   estate investment trusts (REITs),       .04 / (1 – .37) = .0635, or 6.35%. In terms of the amount of income she’ll
n	Regulated     investment companies             get to keep, the municipal bond is a slightly better choice. If the municipal
   (RICs),                                        bond is also exempt from state and local taxes, it’s an even better choice.
                                                  But Cheryl also needs to consider factors such as risk and how well each
n	Money      market mutual funds, and
                                                  bond will help achieve her overall investment goals.
n	Certain    foreign investments.

The tax treatment of bond income
varies. For example:                           AMT ALERT! Tax-exempt interest              by other investment expenses. Any
                                               from private-activity municipal bonds       disallowed interest expense is carried
n	Intereston U.S. government bonds is         can trigger or increase AMT liability.      forward, and you can deduct it in a later
   taxable on federal returns but exempt       However, any income from tax-exempt         year against net investment income.
   by law on state and local returns.          bonds issued in 2009 and 2010 (along
n	Interest on state and local government      with 2009 and 2010 re-fundings of           You may elect to treat all or a portion of
   bonds is excludable on federal returns.     bonds issued after Dec. 31, 2003, and       net long-term capital gains or qualified
   If the bonds were issued in your home       before Jan. 1, 2009) is excluded from       dividends as investment income in
   state, interest also may be excludable      the AMT.                                    order to deduct more of your invest-
   on your state return, depending on                                                      ment interest expense. But if you do,
                                                                                           that portion of the long-term capital
   the state.                                  Investment interest expense
                                                                                           gain or dividend will be taxed at
n	Corporate bond interest is fully taxable    Investment interest expense — interest      ordinary-income rates.
   for federal and state purposes.             on debt used to buy assets held for
n	Bonds   (except U.S. savings bonds)         investment, such as margin debt             Payments a short seller makes to the
   with original issue discount (OID)          used to buy securities — generally is       stock lender in lieu of dividends may
   build up “interest” as they rise            deductible for both regular tax and         be deductible as investment interest
   toward maturity. You’re generally           AMT purposes. But special rules apply.      expense. But interest on debt used
   considered to earn a portion of                                                         to buy securities that pay tax-exempt
   that interest annually — even               Your investment interest expense            income, such as municipal bonds, isn’t
   though the bonds don’t pay this             deduction is limited to your net            deductible.
   interest annually — and you must            investment income, which, for
   pay tax on it.                              the purposes of this deduction,             Also keep in mind that passive interest
                                               generally includes taxable interest,        expense — interest on debt incurred
                                                                                                                                        I NV E ST I NG

Keep in mind that state and municipal          nonqualified dividends and net              to fund a passive activity — becomes
bonds usually pay a lower interest rate.       short-term capital gains (but not           part of your overall passive activity
See Case Study II.                             long-term capital gains), reduced           income or loss, subject to limitations. ❖

                                                                                                                                        11
The TCJA colors the 2018
                   real estate tax landscape

                   T
                         here are many ways you can maximize the tax benefits associated with owning        allowable, without needing to apportion
                         a principal residence, vacation home or rental property — or maintaining a         them between personal and business
                         home office. Tax planning is also important if you’re planning to sell your        use of your home.
                   home or other real estate in 2018. And the Tax Cuts and Jobs Act (TCJA) changes
                   the tax picture with new limits on some home-related deductions, enhancements            Home rental rules
                   to depreciation-related breaks and changes to the interest deduction for businesses,
                                                                                                            If you rent out all or a portion of your
                   including real property businesses.
                                                                                                            principal residence or second home
                                                                                                            for less than 15 days, you don’t have
                   Home-related deductions                     TCJA effectively limits the home equity      to report the income. But expenses
                   The TCJA includes many changes              interest deduction for 2018–2025 to          directly associated with the rental,
                   affecting tax breaks for home ownership.    debt that would qualify for the home         such as advertising and cleaning,
                   Consider these itemized deductions in       mortgage interest deduction.                 won’t be deductible.
                   your tax planning:
                                                               Home office deduction                        If you rent out your principal residence
                   New limits! Property tax deduction. For     Employees can no longer deduct               or second home for 15 days or more,
                   2018–2025, the property tax deduction       home office expenses, because of             you’ll have to report the income. But
                   is subject to the new $10,000 limit on      the suspension of miscellaneous              you may be entitled to deduct some
                   combined deductions for state and local     deductions subject to the 2% of AGI          or all of your rental expenses — such
                   taxes. (See “What’s new!” on page 4.)       floor. (See “What’s new!” on page 4.)        as utilities, repairs, insurance and
                   Higher-income taxpayers owning                                                           depreciation. Exactly what you can
                   valuable homes in high-property-tax         If you’re self-employed and your home        deduct depends on whether the home
                   locations will likely see a huge drop in    office is your principal place of business   is classified as a rental property for
                   the federal tax benefit they receive from   (or used substantially and regularly         tax purposes (based on the amount
                   their property tax payments.                to conduct business) and that’s the          of personal vs. rental use):
                                                               only use of the space, you generally
                   New limits! Mortgage interest               can deduct a portion of your mortgage        Rental property. You can deduct
                   deduction. You generally can deduct         interest, property taxes, insurance,         rental expenses, including losses,
                   interest on mortgage debt incurred          utilities and certain other expenses, and    subject to the real estate activity
                   to purchase, build or improve your          the depreciation allocable to the space.     rules discussed at right. Property
                   principal residence and a second            Or you may be able to use the simplified     tax attributable to the rental use of
                   residence. Points paid related to           method for calculating the deduction.        the home isn’t subject to the new
                   your principal residence also may                                                        $10,000 limit on the state and local
                   be deductible. For 2018–2025, the           Using the simplified option, you can         tax deduction. You can’t deduct any
                   TCJA reduces the mortgage debt limit        deduct $5 per square foot for up             interest that’s attributable to your
                   from $1 million to $750,000 for debt        to 300 square feet (maximum of               personal use of the home. However,
                   incurred after Dec. 15, 2017.               $1,500 per year). Although you can’t         you can take the personal portion of
                                                               depreciate the portion of your home          property tax as an itemized deduction
                   New limits! Home equity debt interest       that’s used as an office — as you            (subject to the new $10,000 limit).
                   deduction. Before the TCJA, interest        could filing Form 8829 — you can
RE A L E S TAT E

                   was deductible on up to $100,000 of         claim mortgage interest, property            Nonrental property. You can deduct rental
                   home equity debt used for any purpose,      taxes and casualty losses as itemized        expenses only to the extent of your rental
                   such as to pay off credit cards (for        deductions to the extent otherwise           or other passive income. Any excess can
                   which interest isn’t deductible). The                                                    be carried forward to offset rental income

12
in future years. You also can take an item-    some negative tax consequences. (See          the TCJA, real estate businesses that
ized deduction for the personal portion of     “Passive activities” on page 10.)             elect to deduct 100% of their business
both mortgage interest and property taxes,                                                   interest will be ineligible for bonus
subject to the applicable limits. In some      To qualify as a real estate professional,     depreciation starting in 2018.
instances, it may be beneficial to reduce      you must annually perform:
personal use of a residence so it will be                                                    2. Enhancement! Section 179
                                               n	More  than 50% of your personal            expensing election. This allows you to
classified as a rental property.
                                                  services in real property trades or        deduct (rather than depreciate over a
                                                  businesses in which you materially         number of years) qualified improvement
Home sales                                        participate, and                           property — a definition expanded by
When you sell your principal residence,        n	More                                       the TCJA from leasehold-improvement,
                                                        than 750 hours of service in
you can exclude up to $250,000 of gain                                                       restaurant and retail-improvement
                                                  these businesses during the year.
($500,000 for married couples filing                                                         property. The TCJA also allows Sec. 179
jointly) if you meet certain tests. Gain       Each year stands on its own, and there        expensing for certain depreciable
that qualifies for exclusion will also be      are other nuances to be aware of. If you’re   tangible personal property used
excluded from the 3.8% NIIT. (See              concerned you’ll fail either test and be      predominantly to furnish lodging and
page 8.) To support an accurate tax basis,     subject to the NIIT or stuck with passive     for the following improvements to
maintain thorough records, including           losses, consider increasing your hours        nonresidential real property: roofs,
information on your original cost and          so you’ll meet the test. Keep in mind that    HVAC equipment, fire protection and
subsequent improvements, reduced by            special rules for spouses may help you        alarm systems, and security systems.
any casualty losses and depreciation           meet the 750-hour test. Warning: To help
claimed based on business use. Warning:        withstand IRS scrutiny, be sure to keep       Under the TCJA, for qualifying property
Gain that’s allocable to a period of “non-     adequate records of time spent.               placed in service in tax years starting in
qualified” use generally isn’t excludable.                                                   2018, the expensing limit increases to
                                               Depreciation-related breaks                   $1 million (from $510,000 for 2017),
Losses on the sale of any personal resi-                                                     subject to a phaseout if your qualified
dence aren’t deductible. But if part of your   Three valuable depreciation-related
                                                                                             asset purchases for the year exceed
home is rented out or used exclusively for     breaks are available to real estate
                                                                                             $2.5 million (compared to $2.03 million
your business, the loss attributable to that   investors:
                                                                                             for 2017). These amounts will be
portion may be deductible.                                                                   adjusted annually for inflation.
                                               1. Enhancement! Bonus depreciation.
Because a second home is ineligible for        This additional first-year depreciation
                                                                                             3. Enhancement! Accelerated depre-
the gain exclusion, consider converting it     is available for qualified assets, which
                                                                                             ciation. This break allows a shortened
to rental use before selling. It can be con-   before the TCJA included qualified
                                                                                             recovery period of 15 years — rather
sidered a business asset, and you may          improvement property. But due to a
                                                                                             than 39 years — for “qualified improve-
be able to defer tax on any gains through      drafting error in the new law, qualified
                                                                                             ment property.” This is a much broader
an installment sale or a Section 1031          improvement property will be eligible for
                                                                                             property category than the one the
exchange. Or you may be able to deduct         bonus depreciation only if a technical
                                                                                             break applied to before the TCJA.
a loss, but only to the extent attributable    correction is issued, which is expected.
to a decline in value after the conversion.    (Check with your tax advisor for the latest
                                               information.) When available, bonus           Tax-deferral strategies
                                               depreciation is increased to 100% (up         It’s possible to divest yourself of appreci-
Real estate activity rules
                                               from 50%) for qualified property placed       ated investment real estate but defer the
Income and losses from investment real                                                       tax liability. Such strategies may even
                                               in service after Sept. 27, 2017, but
estate or rental property are passive by                                                     help you keep your income low enough
                                               before Jan. 1, 2023. For 2023 through
definition — unless you’re a real estate                                                     to avoid triggering the 3.8% NIIT and
                                               2026, bonus depreciation is scheduled
professional. Why is this important?                                                         the 20% long-term capital gains rate.
                                               to be gradually reduced. Warning: Under
Passive activity income and losses have                                                      Consider these deferral strategies:

                                                                                             Installment sale. An installment sale
   WHAT’S NEW!
                                                                                             allows you to defer gains by spreading
   The TCJA limits interest deduction                                                        them over several years as you receive
                                                                                             the proceeds. Warning: Ordinary gain
   Subject to some restrictions and exceptions, under pre-TCJA law interest paid             from certain depreciation recapture is
   or accrued by a business generally was fully deductible. Under the TCJA,                  recognized in the year of sale, even if
   for tax years that begin in 2018 or later, businesses generally can’t deduct              no cash is received.
   interest expenses in excess of 30% of “adjusted taxable income.”
                                                                                             Sec. 1031 exchange. Also known as
   Taxpayers (other than tax shelters) with average annual gross receipts of                 a “like-kind” exchange, this technique
   $25 million or less for the three previous tax years are exempt from the                  allows you to exchange one real estate
   interest deduction limitation. Some other taxpayers are also exempt, includ-              investment property for another and
                                                                                                                                            RE AL E S TATE

   ing real property businesses — but only if they elect to continue to fully                defer paying tax on any gain until you sell
   deduct their interest. And if they make the election, they’re required to use             the replacement property. Discuss the
   the alternative depreciation system for real property used in the business.               limits and risks with your tax advisor. ❖

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