Gainskeeper ™ is a little program keeps tracks of stock cost basis, and the profit and loss. Scottrade provides this service to its customers. This program is not without problems (for me), such as mess up positions and long/short term profit/loss. It seems to me the program improved quite a bit lately, or it could be that now I learned how to use it. Another interesing program (or web site) is cakefinancial, which can keep track of your 401k, IRA and stock brokrage accounts from various financial institutions. Walt Mossberg did a good introduction on this lately.
Back to Gainskeeper. The main thing I pay attention to is: big gainer and big losers. Here is how I used it. Go to Realized Selling Acitivity (Summary), select year (2008). Last year, we all know it’s a terrible market. Here is my big losers (loss > $1,000):