I’M PONDERING WHETHER to make my biggest transaction in four years—and it might be the trickiest financial decision I’ve ever made. My quandary: Should I take advantage of today’s low tax rates to convert a big chunk of my traditional IRA to a Roth?
This financial navel-gazing was sparked by an article by John Yeigh, one of HumbleDollar’s contributors. As John pointed out, you can now have a much higher annual income and still avoid the top federal tax brackets,

“FINANCIAL WRITERS always seem to assume everybody’s married.” That’s a complaint I’ve heard more than once—and it came to mind as I reviewed our 2018 tax return.
That tax return reflected the impact of 2017’s tax law, which—among other things—roughly doubled the size of the standard deduction, while capping the itemized deduction for state, local and property taxes at $10,000. One result: Many couples now get little or no tax benefit from either the mortgage interest they pay or the charitable contributions they make.

THE NCAA BASKETBALL season concludes every year with the March Madness playoffs. Many Americans engage in bracketology—trying to figure out which teams will get knocked out in each round and which will advance. Warren Buffett even offers an annual bracket-picking challenge, where Berkshire employees can win $1 million a year for life.
This year, however, Americans with substantial retirement accounts might also want to try another form of bracketology: studying the 2017 tax law—and asking whether it offers a unique opportunity to convert hefty amounts of traditional IRA money to a Roth IRA.

FEDERAL RESERVE Chair Jerome Powell appeared before Congress late last month and spoke in serious terms about the country’s debt situation. It’s worth understanding what Powell said—and how that might impact your investments.
Powell’s message: “The U.S. federal government is on an unsustainable fiscal path.” Specifically, “debt as a percentage of GDP is growing, and now growing sharply, and that is unsustainable by definition.”
Powell’s remarks mirrored those of the Congressional Budget Office (CBO).

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.

IF YOU’RE GOING TO form one new financial habit this year, make it good recordkeeping. A system that’s easy to follow will improve your financial life both today and for years to come. With all of the annual investment statements and tax documents you’re about to get, this is a great time to start.
Whenever I go to my mailbox, I’m on the receiving end of countless advertisements, credit card offers, insurance notices and more.

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.

I BEGAN WORKING for my father at age 12. He and his brothers run a sign manufacturing business that was co-founded in 1947 by my grandfather. The first few years, I cleaned pickup trucks, swept floors and took out the trash. When I got my driver’s license in high school, I started running errands for the business—better known as a gopher. As a finance major in college, I was able to work my way into the office,

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.

WHAT’S YOUR FAVORITE tax rate? This isn’t meant to be a trick question. If you’re like most people, your favorite rate is probably zero.
While a 0% tax rate is great, it isn’t easy to achieve. There’s just a handful of ways to create tax-free income. If you have young children, 529 accounts are a great option. If you earn a high income, you might buy tax-exempt municipal bonds.
And, of course, there are Roth IRAs.

MY 10-YEAR-OLD SON and I had a chance encounter last month with the commissioner of the Boston Police Department. After saying hello, he bent down and offered my son this advice: “Stay in school,” he said, “and listen to your parents.”
Often, the recipe for childhood success is just that simple. Ditto when it comes to managing money. The basic principles are usually pretty straightforward. But there’s one topic that often leaves people with a headache.