“MIND THE DETAILS If you have income coming from different states — say as a consultant, real estate investor or a person stringing together several jobs — the calculation of what to pay and when becomes trickier. You may end up owing different states because not enough or any tax was withheld, said Kim Rueben, senior fellow at the Tax Policy Center. And if you don’t keep up with those filings, you might have to make a large payment to one while awaiting a refund from another. ”
The article also points out that timing is so important, especially when folks exercise stock options or businesses or appreciated securities. For example, if someone sells a business on August 30, he or she would owe taxes on Sept. 15. But if the sale went through Sept. 3, he or she would have until Jan. 15 to make the payment.
The article points out that the IRS divides up the year in a specific (and often unexpected) way- particularly when it asks for quarterly payments. It’s important to talk to your financial advisor about this since the schedule for payments is not what sellers might expect. (For tax purposes, the second quarter runs from April 1 to May 31, the third from June 1 to Aug. 31 and the fourth stretches four months, from Sept. 1 to Dec. 31.)
Your advisor and accountant can construct a strategy that will meet compliance requirements- and consider other issues like how the net investment income tax — an extra 3.8 percent tax on capital gains for higher earners — should be calculated throughout the year.