On the note of programming not being fun anymore, that's exactly why I'm making my secret project that I hope to release very very soon, maybe in a week or so. I want to make programming fun again, in a similar way that pico8 did, but x100.
> I have the same history customizing everything! ... then giving up because life gets busy.
I think this might be why some people have such different experiences. I don't try to customize "everything" - just what needs to be. Like, yeah, I would expect it to be difficult to maintain random Explorer customizations. I would not expect it to be difficult to maintain customization for a popular IDE.
Too much software put host-specific stuff in settings files (like absolute paths) or just are not stable enough in general that it is worth trying to maintain a portable configuration.