Shaggy Sheep.
I have thought things through for as many variables as possible, "winging it" as you put it is not something I like to hang my life on.
I'm just suggesting that to try to write "rules" would be difficult bearing in mind the number of different scenarios.
Thinking things through in advance is the way. Deciding in an instant which scenario applies at the time & which solution to use is difficult to write down.
I did actually describe two different solutions to a similar problem but in different wind conditions. It wasn't a case of "Ill try this & hope it works". Perhaps I tend to come across as gung-ho let's try this, but rest assured, I'm 75 yr old going on 175 & been around a/c on & off since I soloed a T21 in --56.

One hard and fast rule: DON'T TAXI FAST with STRONG TAILWIND in a tailwheel aircraft.
Many years ago, one of our group was told to expedite. He tried - and groundlooped. The undercarriage failed - at the runway intersection.
I have the stick near neutral, and respond as needed with forward stick.