Q. If I sell these stocks at a $30,000 loss and sell my company stock with a $50,000 short-term capital gain, would I only need to pay capital gains tax on the $20,000 net gain (50k - 30k) this year?
A. Yes. You are allowed to off set short term capital gains with other long term losses.
Q. If I repurchase my company stock immediately after selling, would this trigger a wash sale and prevent me from resetting the cost basis on the company stock?
A. No. Wash sale rules do not apply to stocks sold at a gain. The wash sale rule only apply when you sell at a loss.
