Julian Block

THE INTERNAL REVENUE Code doesn’t authorize much relief for investors when they suffer capital losses that exceed their gains. It allows taxpayers each year to offset the excess against as much as $3,000 of their ordinary income from sources like salaries, pensions and withdrawals from IRAs.
What about the unused losses? The law lets investors carry forward such losses and claim them in an identical way on their tax returns in subsequent years, until they’re used up.

GOT A VACATION home? There’s an overlooked tax break if you rent it out—but a potential tax hit if you sell.
First, the tax break: Long-standing rules allow homeowners to completely sidestep taxes on rental income—provided they meet a key requirement: They rent out their cottage or condo for less than 15 days during the year.
That can be a great tax break for those who own dwellings near annual events where rents soar for short periods.

WORKERS TODAY HAVE income taxes and Social Security taxes withheld from their paychecks. But it didn’t always work that way: The withholding system experienced a difficult birth—in the middle of the Second World War.
The wide-ranging 1943 tax act included a provision that authorized withholding. But President Franklin Roosevelt thought the legislation too complicated, so he vetoed it, saying, “The American taxpayer had been promised of late that tax laws and returns will be drastically simplified.

YOUR INVESTMENT holdings might include an asset that’s dropped in value since you bought it. Still, you have great hopes for the investment: While you’d like to sell and get the tax loss, you really hate to part with your old friend. Should you instead sell it to your spouse or your child?
You can usually claim losses on investments when you sell them. But IRS code section 267 generally disallows deductions for losses on sales to certain family members and other related parties.

WANT TO CUT YOUR tax bill for this year and next? The main thing is to act—or not act—before Dec. 31, while there’s still time to take advantage of tax angles that can generate dramatic savings.
Once we’re beyond Dec. 31, it’s generally too late to do anything but file Form 1040 on the basis of what took place the preceding year. There are a few exceptions. For instance, early in the year, you can still make deductible contribu­tions to some tax-deferred retirement accounts,

SAY “1040” AND MOST of us think of the income tax returns we file each year on April 15. But it’s only because of chance that we fill out 1040s, instead of 1039s or 1041s: That number was up next in the sequential numbering of forms developed by the Bureau of Internal Revenue, the predecessor of today’s IRS.
It all began on Jan. 5, 1914, when the Department of the Treasury unveiled the new Form 1040 for tax year 1913.

IRS AUDITS ARE usually uneventful. Auditors ask taxpayers to produce receipts, canceled checks and similar documentation to verify deductions and other facts and figures. When taxpayers come up with the required substantiation, examiners move on to other audits. In fact, the feds frequently close cases without exacting extra taxes—and sometimes they even authorize refunds.
But things aren’t always so friendly.
Be concerned when an IRS investigator walks in unannounced at your home or office and asks to see your records.

LONG EMBEDDED IN the federal tax code is a provision that provides important advantages for people who sell inherited stocks, real estate or other investments that have appreciated in value and are held outside retirement accounts.
In tax lingo, the basis (the starting point for measuring gain or loss) of inherited assets “steps up” from their original basis (cost, in most instances) to their date-of-death value. It’s as if the inheritors had bought the assets that day.

MANY OF MY CLIENTS volunteer to perform chores for religious institutions and other charitable organizations. I remind them that volunteers qualify for tax breaks. Their itemized deductions include what they spend to cover unreimbursed out-of-pocket outlays—though there are limits to the IRS’s generosity.
I caution clients not to count on deductions for the value of the unpaid time that they devote to charitable chores. Let’s say the prevailing rate for the kind of services they render is $100 per hour and they spend 100 hours to render those services during the year in question.

OWNING A HOME IS getting more expensive, thanks to the Tax Cuts and Jobs Act (TCJA) enacted in December 2017. The new law is the most comprehensive overhaul of the Internal Revenue Code since the Tax Reform Act of 1986. The legislation includes provisions that curtail long-cherished write-offs for mortgage interest and property taxes.
It also abolishes deductions for casualty and theft losses claimed by individuals whose homes, household goods and other property suffer damage due to events like burglaries,

RECENTLY, I STARTED advising three entrepreneurial brothers who are the controlling shareholders of three companies with several hundred employees. All of their companies are presently short of operating cash and unable to borrow from banks or other conventional sources. Without quick infusions of funds, they’ll likely go under.
They won’t be able to pay skittish suppliers who refuse to extend additional credit, even if the brothers guarantee payment. Nor will they be able to meet payroll for employees.

SOME OF MY CLIENTS incur hefty medical expenses for themselves and family members. I tell them not to expect too much help from the IRS when it comes to deducting such expenses—unless the costs are well into five figures.
To deduct medical costs, taxpayers have to forego the standard deduction and instead itemize on Schedule A of Form 1040. Their expenses also have to be for bills that aren’t covered by insurance or reimbursed by employers.

THESE BEING THE TIMES they are, I frequently field queries from clients who are asked for loans by relatives or friends. These would-be borrowers plead their inability to come up with the down payments for homes or who want to launch “can’t fail” business ventures. Suppose, as so often happens, the loans go sour and the borrowers’ last messages mention their entry into witness protection programs.
I remind wannabe lenders who intend to stake friends or relatives to familiarize themselves beforehand with long-standing tax rules.

I HAVE A CLIENT I’ll call Irene. She became a widow in April when husband Henry died.
Like most married couples, they held title to their home in joint ownership with the right of survivorship. In plainer language, this means that co-owner Henry’s death results in his loss of all ownership in their dwelling. Surviving co-owner Irene automatically acquires all ownership in it.
Irene is uncertain what to do with her highly appreciated home.

THE TAX LAW RELIEVES most Social Security recipients of income taxes on their monthly checks. But it requires middle- and upper-income households to count up to 85% of their benefits as reportable income. Sound punishing? It can be especially punishing for couples who are cutting the knot—but they may live happily ever after.
Taxes on Social Security benefits are triggered when recipients’ MAGI exceeds specified amounts. MAGI is an acronym for modified adjusted gross income (and not the term for the three wise men who bore gifts to the infant Jesus).