For me my upgrade path has been finding balance between warmth and dynamics/detail.
It’s looks something like this: find satisfaction (Raven Nighthawk + Tekton), get upgrade bug seeking more dynamics, get more revealing gear (Ma 352), feel fatigued, buy new tubes (Telefunken) and speakers (SF Olympica); want more dynamics (Mc 601 + c50), I immediately get tube pre because of fatigue (c2300), still too sharp (new tubes and DAC); excellent balance, but of course sell speakers, new speakers too revealing, buy Cardas cables to replace Wireworld (ahh just right for now, but may be a little more revealing might be nice).
And oh yeah, working on fixing the damn room problems!
Chasing the unicorn.
Anyone else doing this back and forth?