Has anyone made the jump to $uper High end and were disappointed?

Ayon Audio (USA Tube Audio) has classified ads here on audiogon for $25,000 amps (plus other items lower in price). There must be a decent market for such since the ads are everywhere here. I purchase items blind thru the internet since there’s nothing, outside of HT gear, locally to hear in person. Of course, I always make sure there is a good return policy. With that, the stuff I buy is $4000 and under.

I wonder how disappointed a dealer would be to have someone purchase such a high priced (the $25,000 Ayon amp) item only to have it returned. Plus, how cooperative the dealer would be. That’s $25,000 anyway you look at it (a lot of money). I guess that’s the waters the dealer chose to swin in.

Some of the high priced items, like D’agostino, are beautiful to look at and I am sure they sound fantastic

I've never heard Ayon sound good but have heard D'Agostino sound phenomenal. The lesson here is that the sound is in the ear of the beholder. What is most important is how it sounds to YOU.

Spending more $$$ is no guarante for better sound. If you make smart choices along your personal audi journey you will be able to enjoy what you love even more. A higher resolving system can be more rewarding BUT it can also make things worse when you suddenly hear a weak link that was burried before. Working on each weak link can be very rewarding when you manage to achieve improvements. It is like an endless very personal puzzle. And I agree with Robert Harley that the better (not necessarily more expensive) the system gets the larger the reward from small improvements. The oposite of diminishing returns is what happens, when the resolution of your system allows you to hear a significant difference just by changing a minor component. Just throwing big $$$ at it does not at all guarantee satisfaction!

Throwing - no, but super sound is expensive even if you buy used. Let's not fool ourselves.

Speaking of super high-end, $4000 only buy used/demo cable or used cartridge or rack, though some advocate that $500 vintage cartridges can be at least just as good. 
I will never be operating at this level, I think just high end will be satisfactory. And I won't need a lot of money for that, $50k or so for everything, I guess. But of course if I want custom headblock for Studer deck and outboard custom tube playback head amp, and something like Herzan active isolation platform, that will be extra.