I am typically not very aggressive with my strikes on sold puts, but sometimes the price moves a lot, and as such I also had some 730p that I rolled through the drop into the $500s over the last months, finally closing them out on Friday. I never tried to improve the strike, as I had confidence in the underlying price improving. Despite going $150 ITM I was able to find moments of high IV and on average was able to roll them for $8 premium each during the 8 weeks I held them, but the low was around $4 as I recall. So basically an average of 1% return every week over that large drop. (I also sold more at much lower strikes after the drop for better premium) It is the first time the stock price moved that far against me.Anyway - some experiences this year (Feb to now):
I've had short puts go $150 ITM. That position is still alive, rolling for a small strike improvement and credit, even when $150 ITM. It's also about 2-3 months old and hasn't generated meaningful income for most of that time. And it got there first by generating income on the share run up to $900 (when it generated a lot of income; it's worked out). It's down to a $770 strike (from $820 or so) and has been generating small credits each time I roll it. At $150 ITM I had to roll 2 weeks at a time to get movement. I've also rolled 4 weeks at a time as I view the purpose of a DITM roll being to buy time. The strike improvement and minor credit are secondary consideration with strike improvement being most important (these are my 'rules' - you might develop different 'rules').
I'd say that DITM starts around $50 to 70 ITM these days. Pretty sure that as IV goes down, the ITM number will get closer and closer to the share price.
And it looks like I'm going to have some ~$30 ITM positions to roll this week - I haven't had experience that far ITM to see strike improvement / credit. I'll have a better idea later in the week at this closer level and I'll post those position rolls when I do them.
I will wait and see this week. Hopefully the market will digest the earnings over the next couple of days and by Friday I will likely enter into another position for next week. I've generated enough cash to add 275 shares to my long term holdings over the past 3 months, so I've been generally pleased with my results, .