Down grading with better /= sound

I tried an older pair of Shahinian Obelisks in my system and was astonished to find them rather comfortably more satisfying than my Alon Circes with Thunderbolt subwoofer and custom made crossovers. The Circe setup cost $15,000 while the then current model of the Obelisk was going for in the neighborhood of $4000. I subsequently got a pair of Shahinian Hawks, at the time about $7000, which are even now filling my life with gorgeous music.
I must say it was very hard accepting the "devaluation" of my system but love triumphed over pelf and I have never looked back.

like some fellow Agon members I bet. I have upgraded with worse sound!

At least 3 times!

I have downgraded several times in the last 30+ years. Though I cannot say that I got better sound, I can say that I have gotten pretty damn close for a lot less money.
I'm very happy with my current system, and I've pulled over $20K out of my system after expenses, for other life choices.
I've found that with tube rolling, and careful selections with power cords/cables I'm up to about 98% of my former rig's sonics for about 65% of the cost.

Cheers,
John