You can teach your ears to hear better by listening critically, to both live and recorded music. A mindful process becomes matching the gear you experience with what your increasingly educated ears are telling you. I think the more you learn and move up the fewer new gear experiences you will need, and the more you will enjoy them. After a few years of doing this, now when I go to audio shows I can usually determine if it's worth it to stay in a room or not within two minutes--sometimes it's the gear and sometimes it's the room, but it works out to the same choice about whether to stay or leave. And the best always means coming back later to listen again. If you continue to try out dozens of different audio equipment over many years you aren't listening in a productive way.
But if you are just having fun instead of expanding your audio understanding, then what the hell, why not do it?
But if you are just having fun instead of expanding your audio understanding, then what the hell, why not do it?