The audio gear has been acquired over a 23-year period. When my wife and I find something we like, we tend to keep it until it is beyond repair, or it has been replaced by a piece that sounds noticeably better at an attractive price point. We've moved from 45's and LPs to tapes to CDs to streaming to a newer turntable to listen to our vintage LPs and a few newer ones. Most of our listening is acoustic music, classical and jazz, with an occasional rock album.
My wife and I both play instruments: she the flute and I the piano. We play for recreation and attend live classical and jazz concerts, from large symphonic works to chamber music and piano solos, from jazz vocalists with large jazz bands to piano trios. Our goal with our audio gear has been to have a system that faithfully reproduces the timbre of instruments, the tone of vocalists, provides some sense of the venue and its acoustics, and adds and detracts as little as possible from the original performance. While it's impossible to recreate the sound of the original venue, we find our system comes reasonably close to reproducing the instruments in a manner that is realistic and consistent with our recollections of live performances. Sure there are better, newer (and older) pieces, but the pursuit of perfection comes at a cost and detracts from our primary interest, listening to music.
Enjoyed your description. My approach is also similar, trying to achieve timbre and tone that’s seductive, real and tactile. And I look for this in acoustic or amplified instruments, as well as electronic synthesis.
Similar to you, I believe seeing live music regularly can set a baseline for what to listen for — even without having to emulate the sound of a venue.