Does it ever end?

I can relate to the OP's thoughts, I'm not sure it will ever completely end because technology advances and the allure of something "better" will always be intriguing. I think I'm close to the end of "big"  upgrades. The key for me was finding the sound that really checks the boxes for me with the fewest compromises. I could go for bigger and better of that sound, but no longer feel the need for something different. So, given my age, I doubt there will be any more makeovers, but I've thought that before.

To paraphrase Santayana (some say Plato), "Only the dead have seen the end of upgrades."

I have thought multiple times I was done with upgrades, alas not to be.

However, the one thing I have not wanted to update lately are cables. Specially solid silver cables. They take soooo long to break-in, it's a real PITA.

I feel plenty content now, but at a very high cost.

If money is a concern, treat your upgraditis or go broke.

I have a solution. Add another hobby you are just as passionate about (motorcycles for me) and voila! Your disposable audio funds are now redirected.

I completed a big upgrade back in April of this year and I'm at a plateau on which I am quite pleased. Everything is broken in and the music listening is sublime. As ghdprentice said; I'm good for at least the next seven years or so.

I thought it would end when I couldn't find a single bothersome thing and/or achieved the sound quality I'd always dreamed of. This has proven wrong as in recent years adding variety to the listening experience via adding to the collection, now have three amps, two pre's, soon enough another one in plans, two dacs, two phono stages, two turntables to choose from. Not reaching for better just variety.