So, you have never bought gear that you ended up moving along quickly because it didn't work out like you had hoped it would? I can think of a couple i have tried that didn't stay long (Einstein "The Absolute tune" integrated was the last such failure for me)?
No, I only upgraded from bought gear naturally, not because anything would have been a failure or mismatch.
There is one exception in 3 decades of my audiophile path: the Denafrips Terminator DAC, which I knew was a high risk proposition. Knowing that, I only took the risk after negotiating with the importer a 10 % restocking fee, which he did not usually do. I was initially happy with it until I changed the preamp in my system (I got an Octave HP 300 SE demo in house *)) which revealed a synthetic tone that was not obvious with my Pass B1 buffer. So I returned it with one day to go into the end of the 14 day period. It was an expensive audition ($ 500 with return shipping) but it was worth it to me, I learned a lot.
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*) I then bought the better model of the Octave, the HP 700, which I am super happy with, the end game preamp for me.