I get 'The Nervosa' from time to time, but whether it's just because speakers are a pain in the balls to sell, move & change or it's even harder to find the right speaker, I find it's the speakers that last longest, followed by amps.
It takes me a longtime to both research & find the *right* speakers and a very long time to commit to changing them.
My Vandersteen 2Ci's, Thiel 3.5's, Maggie 3.6's and B&W 802 Matrix's over have seen *dozens* of luscious and a few not so luscious preamps over the last 30ish years. I'm a preamp whore. Love a few different sounds. Love tubes, then I love leaving a nice, hot SS on 24/7 again- it's shameful.
I've probably had a half dozen preamp switches in the last three years. I'm in the middle of one right now.
Amps, again, less than a half dozen- that's another thing. When you get a good one, you just stick with it and dick around elsewhere. Same for DAC's. I hung on to my CAL Sigma 2, which was so 12AX7 tube rolling responsive, for a very long time. I still think about how much pleasing music I used to get through that beauty. I might even retro digi-fit a new one. That was a lovely DAC.