Please learn from my mistakes in tax planning.
1. If you own stocks, bonds, or mutual funds, keep careful records of the following for each purchase or mutual fund distribution:
a) The date
b) How many shares were purchased
c) The net cost
I probably spent 80% of my time researching capital gains distributions. This was a major pain.
2. DO NOT GIVE A GIFT OF SECURITIES THAT HAVE A CAPITAL LOSS! If you want to gift those securities, sell them and gift the proceeds as cash. Giving a gift of securities is complex, but it offers some tax sheltering opportunities.
3. Try out TaxACT tax preparation software. It is free to try, and the deluxe version is a fantastic value.