Here is my homework problem that I need some help with:

Question

"A taxpayer is considering selling 100 shares of stock. The current market price is $7,500. Which shares should the taxpayer instruct the broker to sell, and what are the tax consequences of this selection if the taxpayer owned the following shares in the company?"

Certificate # Date Acquired # of Shares Cost
CR642 4-11-77 300 $15,000
DO1111 9-10-82 100 $9,000
EA002 8-13-84 100 $6,000

Answer 1

I would sell the shares purchased in 1982, which will involve a (long term) capital loss of $1500. There may have to be offsetting capital gains elsewhere in the portfolio (or no other capital losses), to obtain an immediate tax benefit.

I could be wrong.

See
http://www.irs.gov/newsroom/article/0,,id=106799,00.html