....this is something I'm a bit unclear about. Any reading you can suggest on liquidity regarding contract expiry?
The CME website has volume for both contracts, I usually switch on the Friday as that's when volume begins to switch in earnest.
That's useful that they just spell it out for you like that.Here are rollover dates for the foreseeable...
http://www.cmegroup.com/trading/equity-index/rolldates.html
For US indexes, rollover begins the 2nd Thursday of the expiration month. Expiration is the 3rd Friday of the expiration month, fwiw.
Like speedo, volume usually dictates when to change, usually the Friday, but in all cases, for me, no later than the following Monday. Right now, ES volume is just nearing the 50/50 point. NQ volume however has already shifted.

That's useful that they just spell it out for you like that.
Much thanks to you both!
Here are rollover dates for the foreseeable...
http://www.cmegroup.com/trading/equity-index/rolldates.html
For US indexes, rollover begins the 2nd Thursday of the expiration month. Expiration is the 3rd Friday of the expiration month, fwiw.
You’ve mentioned getting options to *pay* you. I’ve been thinking a lot about your hedging (secrets still secret though)... you have to be doing some sort of collar to get paid. That limits your upside though. 2 otm puts - 1 atm call?