The only time you want to sell puts in the S&P's is when it is the scariest to sell them - when the VIX is 30+ and the market is crashing/correcting. During these periods, out-of-the money put implied volatilties skyrocket and trade at irrational/unreasonable levels - premiums trading much higher than actual realized volatility. Everyone and their mother is panicking to buy them, which is exactly when you want to sell them.
You'll have some sleepless nights, but when the market bottoms out and retraces, you'll be able to buy them back at a massive discount, or just let them go out worthless.
You'll have some sleepless nights, but when the market bottoms out and retraces, you'll be able to buy them back at a massive discount, or just let them go out worthless.