I think you've gottten to the point where a CPA really ought to help you out to ensure (or at least give you the best shot) that you are not runniing into trouble with the IRS-- don't trust the otherwise worthy message boards for this stuff. The IRS (if you trust them) can also send you the rules of the game. The basic deal is this: you can choose to average your cost basis, or to pick and choose to sell the positions with the highest cost basis first to put off your cap gains, but you have to be consistent for all of your positions for the year and keep great records.But hey-- if you don't feel that great about the stock, why hold for 18 months? If they really will let you buy at a discount one day and sell the next (sounds unlikely-- read the fine print), then why not just book the no-brainer gain and re-invest the proceeds in stocks you really believe in?I envy your position. Good luck.
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