[CPLX]

You can't necessarily offset the tax bill from the gains with the tax savings from the loss. That's the horrible "gotcha" scenario that makes everyone worry, and is in fact a real risk in these scenarios.

I looked around to find a overview of how this works with some case study examples, and this is the best I could come up with in 5 minutes of googling: https://www.sharespost.com/docs/the_stock_option_tax_dilemma...