Regarding the repurchases of the ISO and the NSO, I assume both repurchases occurred in 2021, and therefore, you should report both on your 2021 return. Generally, if the ISO or NSO shares remain unvested, upon repurchase a company will pay the original purchase price. A company will pay fair market value for shares that have vested.
Regarding the ISO repurchase, what benefit did you receive, if any, when you exercised the option to purchase shares? For the NSO, it appears those must have vested with you as the company repurchased at the current market price which was lower than your cost basis. So for the NSO repurchase, you can claim a capital loss from the repurchase.
@luludeyang
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