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Suggestion: Look at the possibility of selling the short term loss in one year and the long term gain in another. We are getting close to the end of the year and if you don't have to have the money now you may be able to save a few bucks by taking advantage of the previously mentioned $3000 offset against ordinary income vs. taking the long term gain. For maximum tax advantage you would sell the LTCG this year, pay the taxes, sell the STCL in January and deduct $3000 per year against ordinary income until the loss was exhausted. Much of this depends on what "substantial" is, what tax bracket you are in, whether you expect to take LTCGs in the future, what your plans are for the proceeds, etc., etc., etc.

Suggest you look at Schedule D to see how gains and losses are accounted for. Once you do that it may make it easier for you to determine what your best strategy would be considering your circumstances. One size doesn't fit all.
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