Chapotony Chatano here, internet's busiest hogposter, and it's time for another edition of "Let's Argue", where we're on the internet, we accept your hot takes, unpopular opinions, and tough questions, and we struggle sesh over all of them. Leeeeet's, GO!
I always oscilate between loving and hating the theoretical framework. I think the healthiest approach towards it is as a tool to understand why some progressions work, but not why they should be there. Ultimately it's more like grammar to a language, and true poetry is never grounded in a search for the best application of grammar rules.
For me, if we stick to harmony, a lot of times it's an incidental result of chromatic movement. You can then circlejerk over how I just played an Eb9dim5 and it's functioning like a subdominant tritone-replacement. But, more likely, I just moved this way with the bass, and moved the voicing a bit from what was already there, thinking about where I want to land, and complicated chord machine goes brrr.
That is way better put then I ever could, but that's pretty much exactly how I try to think about it. In my eyes, if something works and sounds good in music, then you don't really need to question it too much even if it doesn't "make sense" when you try to apply the amount of music theory that you do know to it. I always figure it would probably make sense in someone elses eyes that knows more theory than I do, haha.