Ugrade-itis - is there a cure?

It’s a hobby. There is no perfect system. I find that new stuff makes my records sound new again. And really I have audio stuff to listen to music, so if new stuff reinvigorates music I enjoy, it’s a huge win. The new stuff is not necessarily better, it’s just different. I like vintage audio these days so I have a parameter of sound I am going for.  The only reason to stop (other then money of course) is that you’re no longer curious. It happens. 

And as hobbyists, I think there’s always an interest in tinkering, improving, etc.
What helped me was shifting my focus to the records (or whatever your preferred medium is). Lots to learn, lots of music to get played that’s new and different to you and a huge amount of history to the recordings, the artists, etc. You can get all geeky on pressings if you like to improve sonics more.
But, it isn’t just something to keep me busy.
It’s the food for the machinery. And into the maw it goes. Some stuff gets put on a shelf and forgotten (yeah, I do purges every once in a great while) and some stuff becomes part of me.
After all, that’s what we’re chasing this good sound for, right?
It will definitely keep you off the street, and probably help appease those "I need something new/different" blues. Ain't no cure. 

I like to upgrade until i'm looking over a cliff that is impractical to cross: 

eg: I have heard every headphone and headphone amp on earth and the only way to get more is big money electrostatic= i'm done. 
eg: I have bought the latest DSLRs and lenses out there, the only way to improve is to switch to mirrorless= I'm done, 
eg: I just upgraded my dac, speakers, interconnnects, and amp and I'm in listening heaven, but it's possible to improve with a power re generator, it's possible to improve with better cables, it' s possible to improve with a better music server, it's possible.... but i could spend alot of money going nowhere= it's time to stop. 

Tastes often change over time... today you like rock... in 3 years blues... in 3 more years jazz...


No doubt that each change will likely mandate a tweak to optimize the sound for the latest preference.


There is a solution...get a different hobby... one that doesn’t involve music. 

Good subject!
You probably get to a point where buying top grade vinyl pressings is the best way to upgrade - you get better sound and increase your library.