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<< I am totally out of the stock by year end. Can I record the 2 transactions seperatly, or do I have to record it as one transaction with an adjusted cost basis ($500 loss plus the second purchase of $10000 for a cost basis of $10500)??
Either way its a $200 capital loss.
Also, what if the same senario occurs except I also have a seperate long term hold position in the same stock? >>

Report each sale separately. See the instructions for reporting wash sales on page D-2 of the 1040 instructions.

Regarding the second question, if you didn't sell any of your long-term AND you properly identified the shares you were selling at the time of sale, there's nothing to report on schedule D with respect to your long-term shares. (If I misunderstood this question, please clarify.)

Phil Marti
Tax Preparer
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