Originally Posted by keep it simple
Sounds like you're entering the arena of "feel" post dots & classical structure. That, & working with other players is a hill climb much steeper than getting the technical elements down.
Exactly this! I'm not sure it can be taught, as such, but it certainly has to be learned and you've articulated it better than I did.
I have tried with Pink Floyd, I really really have, but everything by them that I've ever heard (ok not all that much, just the Wish You Were Here album and that wretched Another Brick song that you can't avoid no matter how hard you try, and Money) has me reaching for the Off button faster than you can say paradiddle-diddle.