I'll need to sell a couple hundred shares now, so 2 contracts will be for this week. For the others, I'd sell October ATM now, roll when to November? An example would help, pls. I'm not comfortable with taking a read 30DTE. Thx.
Well, it's not easy to say when to roll.
When I got deep ITM with 225CC I already said goodbye to those shares (in my mind).
But then the stock went down and gave me more possibilities.
So when deep ITM I'd wait as long as possible (as long as there's time value in it) to see whether stock goes down.
If it isn't, you let the contract expire, if it is, you can roll one month if the premium is starting to be worth it.
When not ITM, it's obvious to just sit and wait and let time value burn/close for x% gain/...
I started this when someone here said he had been rolling a contract monthly for over a year.
Of course weeklies are more profitable, but the extra premium is not worth the time needed to monitor.
If you want concrete numbers:
5/30: Sold 220 CC 06/09 for 2.01
Cash position: +201
6/07: Rolled 220 CC 06/09 to 225 CC 06/16 for +0.24
Cash position: +225
6/12: Rolled 225 CC 06/16 to 225 CC 06/30 for +4.49
Cash position: +674
6/21: Rolled 225 CC 06/30 to 225 CC 07/28 for +5.94
Cash position: +1 268
07/28: Rolled 225 CC 07/28 to 225 CC 09/15 for +4.94
Cash position: +1 762
08/21: Rolled 225 CC 09/15 to 230 CC 10/20 for +5.89
Cash position: +2 351
So actually it was not my intention at first to roll this one monthly, but the stock price action drove me into it. I tend to seek strike improvement and premium together when possible.
If I just let this go for now (but I'm planning to roll it this week if stock price action gives me a good opportunity to roll to November for extra premium and strike improvement to 235), then these are the possible numbers:
If the contract gets executed, I earned 2 351 premium and 1 000 stock appreciation (cost base was 220).
This would be 3 351 for 5 months or 670.20/month.
If it's OTM on 10/20, then it's 2 351 for 5 months or 470.20/month.
But I repeat, I just plan to keep on rolling this.
Should this go OTM this week, I will be looking at November 235 and around 600 premium.