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I feel like I should add a few things to my other post.

You need to be concerned about two things that you likely aren't aware of, wash sales and multiple position rules.

The short version:

Stocks are general FIFO (first in first out), and you don't average cost basis. If you buy 100 shares at 10 bucks and then 100 more shares at 5 bucks, then sell 100 shares later on, you are selling the oldest shares unless you wrote a letter to your broker telling them you specifically wanted to sell the newer shares. The cost basis of the sale is 10 bucks.

It gets worse:

A wash sale generally happens when you sell an investment for a loss and then repurchase a substantially similar investment within 30 days. This works both ways, i.e. you can't buy some more of a stock you already own, and then sell the older shares for a loss within 30 days either.

I highly recommend you visit the fool tax center for a more complete version.


IANATE (I am not a tax expert) :)

Oh, and good luck, it will be a messy hassle sorting out your trades without good records.
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