Checklist of things to do before the end of 2019

There are many tax-saving steps that can be taken before the end of this year. Here is a list of the
most important actions that should be taken no later than Dec. 31, 2019 to save taxes:

… Realize losses on stock while substantially preserving investment position,

… Convert investment income taxable at regular rates (e.g., interest income) into qualifying dividend

… Arrange with employer to defer bonus until 2020,

… Increase basis in S corporation or partnership to make possible a 2018 loss deduction,

… Use credit card to prepay expenses,

… Take advantage of tax credits such as the solar energy credit (expires in 2019), small business
health insurance credit (not for individuals), domestic activities deduction (not for individuals), and
the research credits (not for individuals),.

… Pay contested taxes to deduct them this year while continuing to contest them next year,

… Put new equipment in service before year-end to qualify for the 100% bonus first-year
depreciation allowance, Vehicles over 6,000 pounds allow for additional deductions.

… Make expenditures qualifying for a business property expensing election,

… Settle insurance or damage claim if this will maximize casualty loss deduction,

… Apply bunching strategy to “miscellaneous” itemized deductions, medical expenses, and other
itemized deductions to increase deductible amounts.

… Increase withholding to eliminate or reduce estimated tax penalty,

… Set up self-employed retirement plan,

… Make gifts taking advantage of the $15,000 gift tax exclusion,

… Watch out for marriage penalty in regard to year-end marriage or divorce plans,

… Consider deferring a debt cancellation event until 2020,

… Decide whether to elect to deduct investment interest against capital gains and/or qualified
dividends, see  .

… Avoid personal holding company tax by making dividend payments,

… Take steps to avoid or minimize income tax on Social Security benefits,

… Structure real estate deal to avoid paying interest on tax deferred under installment method,

… Step up level of participation in business activity to meet material participation standard under
passive loss rules,

… Dispose of passive activity to free up suspended losses,

… Ask employer to increase withholding of state and local taxes to pull the deduction of those taxes
into 2020,

… Accelerate a big ticket purchase (such as a boat or car) into 2020 to qualify (if the taxpayer
itemizes) for state and local sales tax deductions instead of state and local income taxes.