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I recently sold some AOL and AMZN for literally $10,000's of thousands of dollars of profit in just over 30 days. First, I foolishly (small "f") sold it last Tuesday. I realize I have a short term tax gain hit coming. Is the sale itself the taxable event (in which case I owe the taxes in April) or is it the T+3 funding date that triggers the taxable event, in which case I realize the gain in 1999 and get a year repreive.

Second, I owned 100 shares of AMZN for 30 days straight. So, naturally, I had a near double on a $20,000 "investment". I then sold 100 shares and bought back 100 shares on the same day (regretting the ill-conceived sale). Can I match the buy and sell orders of the same day (which amounts to a $300 gain) with each other and defer the gargantuan profits I have on the older holdings, or must I match the older holdings with the sale order?
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