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Your strategy will not have the advantage that I suspect you think it will, because losses and gains, whether long or short term, are balanced against each other. If you fill out a mock Schedule D on Form 1040, you'll see how it works.

My suspicion is that you were thinking you would balance your short term losses against ordinary income, and then pay tax on the long term gain at a lower tax rate. It doesn't work that way. Maybe it should (write your Congressman, especially if he's a Republican), but it doesn't.
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