In regards to stereo gear, I think that's just a part of the journey for most people. Some people finally settle on a system and a sound that brings them joy whenever they sit down to listen to it, and others are always tinkering and/or get joy from trying new things. For some people, musical enjoyment comes from the thrill of the chase itself and gaining new audio experiences. No matter the case, and regardless of what kind of gear one tries or prefers, there's no wrong way about going about it IMO. Even the most long and winding journey through this great hobby of ours holds merit. Along that path there is so much to be learned. Not just about the gear itself, but about yourself and your own preferences for gear based on sound, as well as lessons about how you hear sound and the gear you prefer because of that. Those things can only come from one's journey through this hobby, and every one is unique and meaningful for that individual.
As for guitars, I totally agree about the sound of an original PAF-loaded sunburst or goldtop Les Paul. The sound they produce has always been a chase to attain. As it is for countless people who are not able to afford such hallowed instruments. It's arguably one of, if not the hardest sound to replicate with modern pickups and gear. Countless pickup and guitar builders have tried, but an extreme few have ever come close to achieving the indescribable "mojo" that those old guitars and pickups had. It's almost maddening.