Capital gains for 2008 - 2010

I agree that you should not let "the tax tail wag the dog". I don't intend to hold off making a decision on selling any particular investment. What I would do is to look at any stocks or mutual funds in 2008 (09-10 ??), select the one that has appreciated the most since purchase, perhaps buy a similar number of shares 31 days before (or after !) the proposed date of sale. In this way I could capture some measure of the (hoped) for gain and increase my cost basis. Inasmuch as the least amount of taxable income I could possibly recognize in '08 would be in the neighborhood of $

Why worry about the wash sale rule? It only prevents you from taking losses, not recognizing gains. Seth

The point to doing this is not necessarily to sell off a particular asset, but to increase the cost basis of whatever asset class happens to have performed the best. If I have a small cap value mutual fund with a low cost basis, by selling and then repurchasing the same fund I now have a 'stepped up' tax basis for some time in the future when I may want or need to sell.

The point to doing this is not necessarily to sell off a particular asset, but to increase the cost basis of whatever asset class happens to have performed the best. If I have a small cap value mutual fund with a low cost basis, by selling and then repurchasing the same fund I now have a 'stepped up' tax basis for some time in the future when I may want or need to sell.

The wash sale rule only prevents you from taking a loss. You would still report the gain even if you sold and rebought on the same day. Seth