I own 7500 shares of Google at $185, instead of selling and paying CG taxes, I want to sell $400 Dec 26 calls and collect $20 premium. If in Dec 27, stock goes above $400, I will roll those calls to Dec 27 and book capital loss, if it stays below I don’t mind paying CG on $150k (which is kinda free money).
What’s wrong with above? In a way using CC to make income or offset losses.