I just spent about 8 hours doing my 24-year-old’s taxes for her – longer than it took to do my own, because she had wages from employers in three states last year, plus income and losses in family investment partnerships, etc. It took about 100 phone calls and FAXes just to get the numbers. I dont actually mind doing this for her, because otherwise there’s no way she would get it done on time and isnt really informed about the capital loss deductions — I saved her over $1000. But I’m tempted to tell her to go to HR Block next year. At what point do I tell her this is her responsibility?

I would say, several years ago. But not by herself — this is a perfect situation for insisting on mentoring. You say you did it “for her” – if this means she was out somewhere having a nice day while you were doing this good deed, I question whether it was all that helpful. This is practically a one-sentence summary of our whole book: your willingness to help gives you the right to insist she sit there with you and learn how to do it herself in the future!