I will also add, that trading in a taxable account really changes the calculus as well.
Yesterday you could sell a 1000 strike call for 10/15 for $0.23 per share (credit of $23 for selling 1 contract). And according to the volatility at that time, the probability of the strike reaching 1000 within 7 trading days was less than 2%. So it seems like free money.
If we take a binomial model where TSLA can either be 800 or 1001 at expiry, and assuming you can buy the option back for the difference between the strike and the underlying, the expected return of the option is 23 + (0.98*0) + (0.02* -100) = $21. In fact, TSLA needs to go to about $1011.50 before the expected value drops to $0.
But now assume that liquidity dries up and you can't buy the ITM option back. Or the SP reaches a point where you no longer have the cash in your account to buy the option back. Your shares get called away, and suddenly you've created a taxable event in the thousands of dollars that wouldn't have otherwise happened. If you sell the shares at $1000 per share, and put away 25% to pay taxes, and buy back in to TSLA, you've lost 25% of your TSLA holdings you wouldn't have lost otherwise. Expected value (in terms of your portfolio value) drops to 23 + (0.98*0) + (0.02 * -25,000) = -$477