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Tax Time Just Got Easier

By Rich Smith – Updated Apr 6, 2017 at 8:48AM

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And you can thank the IRS.

"Hold the applause. Just send money."

So goes the cheeky old saw. But this week, I'm going to suggest that as Americans prepare to mail the Internal Revenue Service our quarterly estimated tax payments (what? You say you've got a "real" job? Not self-employed? Lucky duck), we also give a round of applause to the folks who just made tax time easier. Not pleasant, mind you. Just easier.

You see, effective Jan. 1, the IRS is about to institute a new rule requiring that brokerages begin keeping track of how much you pay when you buy a stock -- your "cost basis," in accounting parlance. Seems not all of us keep good track of our investing moves. Some of us even toss our brokerage statements in the shredder (imagine that!). And when we do that, we risk forgetting exactly how much we paid for any given stock between time of purchase and April 15.

Result: A lot of hair-pulling, a lot of guessing at the "right" answers, a lot of fingers crossed in hopes we don't get audited (which is currently the only way the IRS has to confirm that the cost basis we state on our income tax returns, is in fact the price we originally paid for our stocks.)

And that's the problem, in a nutshell. The IRS doesn't trust our memories, or our record-keeping skills, and worries we might be tempted to fudge the numbers a bit come tax time. (Or even if we're honest, the IRS fears that in calculating our profits and losses in April, we'll use 20-20 hindsight to pick the most advantageous "tax lots" of stock to have bought and sold, siphoning potential taxes away from a cash-starved Treasury.) So they're sticking Schwab (Nasdaq: SCHW), TD AMERITRADE (Nasdaq: AMTD), E*TRADE (Nasdaq: ETFC), and the rest of the brokerage world with the responsibility -- and expense -- of keeping track of it for us.

New result: Henceforth, when you sell part of your holdings in a given stock, your brokerage will begin asking you which specific shares you're selling. It's going to keep track of this, and of how much you pay when you buy a stock as well, and come tax time a year from now, your annual Form 1099-B will remind you of all your transactions -- to the decimal. (Similar treatment applies to DRIPs and ETFs beginning in tax year 2012, and to options and bonds in 2013.)

How to play it
Brokerages will incur higher costs from the new record-keeping requirements, and face possible fines if they mess up their math homework and send an inaccurate statement to a customer or to the IRS. So this is incrementally bad news for brokerages. Conversely, by simplifying tax time, the new regs are going to decrease taxpayers' need for in-person tax advice from paid preparers. That's bad news for Jackson Hewitt and H&R Block (NYSE: HRB), but I think it's good news for TurboTax maker Intuit (Nasdaq: INTU), because taxpayers could find its software becoming easier to use than ever.

Of course, the biggest winner is you, the individual investor/taxpayer. Merry Christmas from the IRS.

Charles Schwab is a Motley Fool Stock Advisor recommendation, but Fool contributor Rich Smith does not own shares of any company named above. Fools may not all hold the same opinions, but we all believe that considering a diverse range of insights makes us better investors. The Motley Fool has a disclosure policy.

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Stocks Mentioned

TD Ameritrade Holding Corporation Stock Quote
TD Ameritrade Holding Corporation
AMTD
Intuit Inc. Stock Quote
Intuit Inc.
INTU
$395.80 (0.47%) $1.83
E*TRADE Financial Corporation Stock Quote
E*TRADE Financial Corporation
ETFC
H&R Block, Inc. Stock Quote
H&R Block, Inc.
HRB
$42.32 (-3.42%) $-1.50

*Average returns of all recommendations since inception. Cost basis and return based on previous market day close.

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