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>When I buy stocks at two different prices, are the
purchases weighed?

It makes no sense to do otherwise. However, if you sell a specific lot of shares, you can use the actual cost as your basis for tax purposes. In your example, if you sold all 100 shares, your basis is (10*$5+90*$6), or $590, with an average (weighted) cost per share of $5.90. However, if you sold only the 90 shares you bought at $6, your basis is $540.

>Is $3000 the most one can deduct as capital gain losses? If you have more than that, it rolls over right?

You can deduct as much as you have to offset capital gains; however, only $3000 can be used as a deduction against ordinary income. Thus if you have capital gains of $10000, and losses of $15000, you would net zero capital gains, deduct $3000 from income, and still have $2000 left to carry over to the following year, where the process repeats.
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