When is too early to roll CC that are $5 OTM (nine days)?
Such a simple question, such a difficult answer. NOT-ADVICE of course but....
I'm primarily in it for income in retirement, so a question I ask myself is whether a given choice is consistent with an income / dividend mindset. That frequently guides me to decisions that at least appear to be more conservative on the surface.
This particular question - I'd let it ride unless I was particularly worried about the move AND I knew I wasn't going to be able to monitor and react if it kept going against me.
So one thing I would do, and frequently, as you're still getting a feel for these is to setup a roll to see what's available. Setup a roll and see what you can get to for an additional week; maybe also 2 weeks, etc... What I remember is you get the best roll ATM, a really good roll while still slightly OTM or slightly ITM, and the quality of the roll falls off pretty rapidly at our current low IV situation.
So the benefit of rolling early is that you buy time while the roll is good as a mitigation for a disastrously big move against you. The downside is that you also increase the DTE which expands the window for that disastrously big move against you to occur in. There's nothing free
The income / dividend focus leads me to be more proactive about rolling. For me a roll is a defensive / loss management(mitigation) move where I'm trading a week of earning little income, in exchange for a position that I like better than the one I'm in. Losing a week of income is an opportunity cost, and I'm earning so much overall that the lost week isn't a problem.
What is a problem though is a particularly big move against me. Remember that we're making defined reward trades with unlimited risk. A single position going badly against can wipe out months or more worth of gains.
Another thought or criteria that I have specific to cc that you'd like to avoid assignment on - would I rather be assigned on the position as it is, or assigned at the position I can roll to? This works better at 3 DTE than 9 DTE (less time value remaining, better roll available), but the situation is what it is. In general if I could take a slightly ITM and add $10 to the strike along with a $1 credit a week later, that's an assignment I would prefer. And if the shares reverse and the option goes OTM by then, well I earned $1 for that additional week and didn't get assigned.
I can play this particular game a lot
I have my own bias to not get more than 4 (maybe 5) weeks to expiration, and <3 is highly preferable. If I got that far out then I'd have a pretty strong bias towards letting it go to assignment (realizing that it might reverse as we get closer to expiration - these are decisions that can be made every day).