"When entering each sale into TT through the "Stocks, Mutual Funds,
Bonds, Other" section, should I click "I'll enter additional info on my
own" and enter the federal and state tax paid or would that be double
counting?"
That would be double counting and you can't deduct the same taxes twice.
Frequently people are sure that they have to enter the taxes withheld reported by the broker in supplemental information accompanying the 1099-B because their taxes increase dramatically when they enter the sale. In almost every case that's because they use the wrong basis for the sale which is not the $0 reported by the broker. That's not your issue, is it?
Tom Young
