Stock wash sale

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.

Though...an added point of caution here

.....IF you have other long-term gains, the long-term loss will be used against those first, and might result in a larger amount of short-term gain that will be taxed, than you originally planned on.

For example, even if you don't have any other long-term gains from other stock sales during the year, some folks forget that they will get long-term gain distributions from Mutual Funds they own (reported in Box 2a on 1099-DIV forms), which usually happens right at the end of the year (most happen in December), and your planned sales, resulting long-term losses will be used against those Mutual Fund gain distributions first.