puerto rico: I think my main concern is with the Federal tax return. Also, my wife worked in Puerto Rico until September, but didn't work the rest of the year in MA. In PR we don't pay federal taxes, but I've filed federal tax returns when I worked for the US Department of Justice in PR. It's all so confusing.|||See IRS publication 570 (territories).|||Since you have such a complicated situation, I think your money would be well-spent to have a CPA prepare your return this year.