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What to look for from the Republican tax bill, month by month

President Trump delivers remarks after signing sweeping tax overhaul legislation into law on Friday in the Oval Office. (Jonathan Ernst/Reuters)
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On Friday morning, President Trump signed into law the sprawling tax bill that was hastily built out by Republican leaders over the past month. In doing so, he formalized a huge range of changes to how Americans — and American businesses — will pay their taxes.

Given that U.S. tax law was not particularly user-friendly even before the Republican rehaul, we reached out to Manhattan-based tax attorneys Steven and Benjamin Goldburd to explain how the law will affect Americans over the course of the year. Or, really, the next decade.

There are two overarching caveats the Goldburds made clear in our conversation. The first is that much of the detail of the law will be established after the IRS releases regulations stemming from the changes that Congress made — a rolling set of updates that will come over the next year. The second is that, as with any discussion of taxes, your best bet is to actually sit down and discuss your particular situation with a tax professional, instead of relying on the analysis of two attorneys discussing the population as a whole — and filtered through a Post reporter whose expertise with the tax code amounts to knowing generally where his past years’ returns are stored on his computer.

Without further ado: What to expect from the changes to the tax code.

Before the end of 2017

The Goldburds had a few recommendations for changes Americans might want to make now, before the law changes for the 2018 fiscal year.

Property taxes. The law changes how much of the nonfederal tax you pay will be able to be deducted starting in 2018. (This includes state and local taxes.) If you wanted to deduct most of those taxes by, say, paying them now, you’re generally not going to be able to, the Goldburds said — but you can do that with property taxes. Pay next year’s taxes before the end of the year and you can deduct them on your 2017 returns.

Medical expenses. If you have large medical bills that you’ve been paying off, it may make sense to pay more than you normally would before Jan. 1. Changes in the law mean you could see a benefit on your 2017 taxes (paid next April) thanks to a lower threshold for deducting, applied retroactively to 2017. Put more simply: If you pay 7 percent of your income in medical bills, paying 7.5 percent instead will trigger your ability to take a deduction on this year’s taxes. Before the bill was signed, you’d have to get to 10 percent.

Charity. If you generally make small charitable contributions and then deduct those contributions on your taxes, the benefit of doing so will probably decrease on Jan 1.

Why? Filers have a choice between a standard and itemized deductions. Before the new law, some people who gave to charity would itemize those contributions to see a benefit greater than the standard deduction. The new law doubles the standard deduction, so it’s less probable that itemizing those charitable contributions will surpass the benefit from that standard deduction. Giving to charity before the end of the year means you can enjoy the same relative tax benefit from those contributions if you usually itemize the contributions.

Charities that have a lot of small donors, the Goldburds noted, are one of the big losers from the tax bill.

Jan. 1, 2018

The law comes into effect — but the effects won’t be felt immediately.

The Goldburds recommend talking to tax advisers early in the year to plan for how the law affects you. For example, it may be worth it for some people who earn certain types of income to become independent contractors, allowing them to take a 20 percent deduction on that income. But, again: Talk to someone who does this for a living.

Among the changes that begin in January are an expansion of what are known as “529” plans. These were formerly reserved for saving money for college, but the new law expands their use to include paying for K-12 education as well. This will mostly benefit wealthier individuals whose kids attend private schools, but, if that’s you, take advantage.

If you’re looking to buy or refinance a house, be aware that the mortgage interest deduction will be capped at $750,000 as of the first of the year instead of $1 million. If you are planning on buying a new house or refinancing, doing so after Jan. 1 will mean different considerations in doing so.

Another change is the increase in the threshold for the estate tax. If you are a wealthy person who dies on Dec. 31, more of your estate can be taxed than if you die the next day. Take that into account when you are thinking about when you plan to die.

As of the first of the year, businesses will start seeing lower tax rates. The grand theory behind the Republican plan is that this benefit will trickle down to everyone else in the form of new jobs and higher wages. Some stockholders will probably see benefits right out of the gate, as companies buy back stock.

February 2018

In February, the IRS will publish new tax rates. (For individual taxpayers, there are a range of brackets that determine how much is paid. For businesses, it’s much simpler.)

As it stands, your paycheck withholds a certain amount of money to pay your federal taxes. On Jan. 1, the amount that’s withheld will probably be too high, since most people are getting a tax cut beginning next year. But we won’t know until February — when the IRS releases the new rates — how much you’re overpaying. (You’ll get those overpayments back after you file in 2019.)

The upshot is that, once the IRS publishes the new rates, you’ll have less taken out of your paycheck in taxes.

April 2018: Filing your taxes

Not much will be different from when you filed this year, since you’re paying on your 2017 earnings. If you did pay more on your medical bills, though, this is where you’d see that deduction kick in.

Before the end of 2018

Remember how the Goldburds recommended prepaying on your property taxes? Well, it may be worth trying to figure out how to prepay another expense before the end of 2018: alimony payments.

That’s right. If you’re paying money to an ex-spouse, your ability to deduct that payment will end beginning in 2019. So you may want to head back to court and see if you can pay more in 2018 to claim the deduction on that year’s taxes.

Jan. 1, 2019

The Obamacare individual mandate ends, meaning that the requirement that you either have insurance coverage or pay a fine goes away. Now, you may choose to not have medical insurance and not have to pay extra on your taxes.

April 2019: Filing your taxes

You’ll get more money back after filing your taxes this year, thanks to your overpayment in January and February of 2018. The alternative minimum tax also goes up for this filing.


The individual tax cuts expire, unless renewed by Congress. Look for a Post article in late December 2025 articulating what to expect from that point forward.

All of this complexity seems like it is a boon for those, like the Goldburds, in the business of explaining how tax law applies. They were quick to note, though, that while they may get more business from those trying to figure out how the tax code changes apply to them, they are also in the service industry, for which there’s a cap of $315,000 for the 20 percent deduction which means that, uh…

Tell you what. If you’re worried about pass-through businesses and LLCs and whatever that change is for the service industry, go talk to a professional.