The Friday before options expiration is also interesting. There's an attractive amount of premium available on the at-the-money (ATM) calls. Yesterday I spent quite a bit of time closing out out of the money calls (OTM) calls and writing slightly in-the-money (ITM) calls. Since it was a down day I would been better off just closing out the positions early, but that's just hindsight. I think I was able to offset about half the losses with my activities. That would be a good exercise to work through--to find out if that is correct amount I saved. It is also interesting to think about using temporary VIX positions to offset the risk in this. The VIX upticked about 3 points this Friday.
As it turned out, SPY closed below the strike price on the options I held, so I have market risk on a lot of stock on market open Monday. Right now I think there is more downside risk than upside, so I am not just reflexively going to write calls on Monday morning.
The 3 day settlement time is a real pain in the IRA accounts. With the potential of options being exercised I need to be very careful to not run into "free ride" restrictions.
Buying SDS to hedge the SPY position does not work because any price movement above the strike price is not hedged (the option when ITM already nets that out).
Right now I am thinking that just passively writing covered calls is not going to deliever superior results--you miss out on the big up swings without enough downside protection. I like the idea of playing the short term volatility better, or potentially doing a delta hedge using SDS but biasing things towards the upside.