Even before the new tax law, the U.S. tax code provided loopholes and special breaks that favor wealthy real estate investors. Tax experts say they’re often able to claim losses more quickly and easily than other taxpayers. They are also afforded several ways of delaying or avoiding reporting profits to the Internal Revenue Service.
They can fall behind on their debts and still face fewer tax penalties for having the debt forgiven than other kinds of investors, according to Steve Wamhoff, director of federal tax policy at the Institute on Taxation and Economic Policy. Trump took advantage of that, Wamhoff says, when he couldn’t repay debts on his Atlantic City casinos in the 1990s and early 2000s.