Yes, the premiums on the long dated OTM SPY are still historically rich. My long is actually in ES futures and I have managed to sell near OTM calls high enough

Yes, the premiums on the long dated OTM SPY are still historically rich. My long is actually in ES futures and I have managed to sell near OTM calls high enough to not be called away while still defraying the cost of the SPY puts a bit. Any any event, best viewed as sleep at night insurance. I find it helpful to look not at OMG the Vol! but what you are paying as a % of current market for insurance, annualized. For instance, $21 for Dec 22 300 puts on SPY is about 2.75%/yr. Obviously the delta won't go to 1 even in a tank due to vol and time, but it will cover some of the fall in the short term and if it is prolonged, everything below 300.