Your 8 Most Vexing Tax Questions, Answered

Quite possibly, if you had education expenses, significant medical costs or made energy-efficient improvements to your home. Several popular tax breaks that expired at the end of 2017 have now been renewed for tax years 2018 through 2020, (which means you would need to refile your 2018 return to claim it for that year).

Here’s a sampling of those changes:

  • Qualified tuition and fees. Deducting up to $4,000 is possible again for tax years 2019 and 2018 (and 2020), even if you do not itemize elsewhere on your tax return. But this break — which also covers items like textbooks, but not room and board — is subject to income limitations. Married couples filing jointly whose adjusted gross income does not exceed $130,000, or $65,000 for individual filers, can claim the full deduction. Other education tax breaks, including the American Opportunity Credit or the Lifetime Learning Credit, may yield more savings, so you need to run the numbers.

  • Nonbusiness energy property credit. Homeowners who have made their homes more energy efficient starting in 2018 — say, through installing windows or doors — may be eligible for a nonrefundable credit of up to $500 (total, for your lifetime). There are rules and limitations based on the type of improvements made, said Mark Luscombe, principal federal tax analyst at Wolters Kluwer Tax & Accounting..

  • Medical expenses. Until changes were put in place in late 2019, taxpayers could deduct the portion of medical expenses that exceeded 10 percent of adjusted gross income, but only if they itemize. That floor has been reduced to 7.5 percent of income for 2019 and 2020.

  • Mortgage insurance. If you pay mortgage insurance premiums — often a requirement when making a down payment of less than 20 percent — those costs are now deductible in the tax years 2018 through 2020, but only if you itemize. This break phases out for single and married taxpayers filing jointly once their adjusted gross income is more than $109,000.

When high-income couples get in touch with Louise F. Cochrane about buying a home in the pricey San Francisco Bay Area, the conversation often becomes a lament: A married couple can deduct the interest on only the first $750,000 of a mortgage.

What some unmarried couples are now doing, Ms. Cochrane says, is simply not getting married. They file separate tax returns and claim deductions on up to $750,000 in mortgage debt each, even though they use one loan to buy a home together.

Ms. Cochrane, whose office is in Alameda, Calif., offered some advice. The couple should have a cohabitation agreement, which can lead to a fair resolution in case of a split. And she said each partner needs a will and trust, too, if one person wishes to leave half of the home to the other.

Clients have been asking Jennifer Kohlbacher, a Tulsa, Okla., accountant, how they can contribute to charitable organizations while getting the largest tax deductions possible.

The issue arises from the 2017 tax bill, which nearly doubled the standard deduction: It will be $12,200 for single people this year and $24,400 for married people filing taxes jointly, and fewer people are bothering to itemize.

Ms. Kohlbacher advises those making charitable gifts to bunch two years of intended contributions into one, in an attempt to itemize deductions every other year, at the very least. And if you must take withdrawals from an individual retirement account, she says, give straight from the I.R.A., so that the money is not subject to income taxes.

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