I’m going to start answering my own question now that others have chimed in.
For me, DIY was important. I got to make exactly what I wanted. It’s like cooking your own meal. I find I am 100 times less critical of my own speakers than I am of anything I'd buy. Not forcing you to go this route, just explaining my own path.
Giving up on cables. I found pure silver wiring from Parts Connexion that was loads better than basic, and yet good enough. I make my own.
Room acoustics. I found that a lot of the reasons I wanted to keep changing speakers were not solvable by new speakers but by having room acoustics that helped me see through my room.
Giving up on imaging. It’s not that I don’t care about imaging, but given a preference I prefer hearing the acoustic recording space, and smooth tonal accuracy over being able to feel musicians in my room, or attempting to place each violinist. These items are often in conflict and I made my choices. This is also related to giving up on cables. I found too often I was giving up musical experience for imaging.
Kind of related to all of this is I gave up on mining for details. There’s always some piece of gear that accentuates a different band of music than what I own, and for the moment it feels like I would "rediscover" my music all over again if I switched, when all I’m doing is switching one set of highlights for another.