I think I don't quite follow or comprehend the description and its questions, perhaps due to my limited understanding of options trading, especially short selling naked.
However, I would think, in general any work-in-progress adjustment suggested/implemented on currently losing options in naked short positions would not be much helpful (if not getting worse), nor better than simply closing the losing options for cutting loss.
Of course, there could be exceptions (probably in this thread) beyond imagination - that would make a trader one of the best options-sellers on earth!
Just 2 cents!
My understanding is that CS wants to capture time decay, which is a very valid approach, as I done it in the past, and seen how good it actually is. He has covered some of the basic requirements, as in only trading European Style if selling options, as they can only be excercised at expiry.
However, as with all trading, he is trying to come up with a way to reduce his risk, with a strategy that has unlimited risk, and this is not easy, unless you fully understand volatility and probability, for, you are competing with those who spend millions developing software with the best math minds out there.
I think his approach is wrong, and he should be very selective when he sells for time decay, and always cover your naked position with another strike, as this is your stop loss, which you should never trade without.
I done it before, so I know a small bit about it, but as always, I wish I knew then what I now know.
Never tinker with things you do not fully understand, as you will get caught out if you panic, and do not know how to adjust losing positions correctly.
Overall, it is a money maker, that is for sure, but you must know exactly what you need to do when price moves against you, and it then just becomes a matter of time, which is the whole purpose of selling options.
And never get greedy, aka, overtrading
J_S