The Wilt Chamberlain of Audio Gear

The "big dipper" was like no other in one year he  averaged 50pts.,another averaged over 20 rebounds, and one year he even leads the league in assist no one not MJ,not Kareem nor Kobe, or James dominated like Wilt he could do anything he wanted on the court. Sadly his supporting cast in Philly was not up to snuff. 
Russell was not as good no way no how but won 11 championships because he had the other parts that matched his game and they made beautiful music together. 
Somewhere in the above is a core belief of audiophiles about synergistic interactions.

I spent most of my money on alcohol and hookers. The rest I just wasted.

I’ve owned 33 speakers in the last 30 years.

I have owned 26 amps in the last 30 years.

Yes, I have a problem.......

For a few years I'd say I was a "Stephen Curry" but now I'd say I was a "John Lucas".

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?