Treasury Stock tax question

I don’t think it is taxed.

S or C?

Don’t mess with the treasury stock unless you absolutely have to. It changes owners equity and can create a red flag for the IRS to look at basis and the transactions.

Work with an attorney to authorize more shares of stock, create two classes of stock (to fix the “old” stock that was bought out and set that basis as low as you can), new authorized shares then can be issued at another agreed upon value.

You can always authorize more shares of stock but don’t have to necessarily issue them.