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


I'm talking $50,000 and higher amps, speakers, cablesetc. I know there is excellent sounding gear from $100 to infinity (much is system dependent, room, etc). However, just curious if someone made the leap and deep down realize the "expected" sound quality jump was not as much as the price jump. Unfortunately, I'm not in a position to make that jump. However, looking at another forum's thread about price point of diminishing returns got me wondering if anyone had buyers remorse. It's not easy to just "flip" a super high priced component. 
aberyclark
Read whitecamaross’ thread, " My Long List of Amplifiers and My Personal Review of Each!"

He swaps expensive gear like the rest of us change clothes and has his mind blown by his new gear on a regular basis. His cost is on a generally, but not always, upward trend.

I think part of his frequent amazement is the new factor. What sounds amazing to us at first often becomes only ok after we’ve gotten used to it. I think for most of us the way to go is to have a system we like, but is not the ultimate, and a Tidal subscription, and get our kicks discovering new music instead of buying new gear. On Tidal I listen to a lot of music I would never buy and find a lot of stuff that I enjoy.  Maybe not forever, but it's definitely good for a few listens.
I think the only thing I would regret paying for, if I had unlimited money, and spent it on audio equipment, would be music servers. I cannot conceive of a way for a computer system with ethernet and USB to cost over $10,000. Probably not over $5000. That tech goes out of date so fast, and seems like it is really off-the-shelf. I don’t believe the people selling it have the know-how or the technology to justify the price. They don’t have the skill to produce systems that can cost that much. But I don’t have the money, so I just don’t know. Everything else, I would imagine is a joy to own. And I don’t imagine anyone that owns it would say otherwise. I wish I did.  My current everything, with tubes and cables is over 10k so I'm a guppy in a big ocean.  But I’m also an IT professional, so I know computers and data transfer. 

Good point mward.  I am also very reluctant to spend much on digital technology, considering how often it changes and relegates everything before it as "old tech."  
I am aware that all gear depreciates, but it seems that computer tech loses its value as quickly as it gets released.  
Very good cd players can be had used for not too much. As for computer listening, my current super high-end gear consists of $200 Grado headphones. Thinking about adding $300 Oppo dac/headphone amp plus $100 Audioquest cable. Later maybe a jump to Grado RS1 or some HiFi Man phones and better dac/amp. But I have no intention to spend much on this stuff.
I’ve heard numerous times “your system is only as good as the weakest link”

in many of the high $ systems, the material ( music) one listens to is actually the weakest length. Over at Computer Audiophile, people debate the merits of $5000 usb cables. In reality, general industrial grade data cables were used to transfer the master recording data to the cd pressing equipment. The same cables used on all these hi rez music streaming systems using general industrial server hard drives.

Most recording studios are wired to keep out noise more so than audiophile quality. Thus, most studios are wired with Beldon/ Canare level wiring. Plus, using general data cables and hard drives ( although Glymph caters to the audio/ video industry, i would not consider them audiophile since same drives are used as in any orher system)

At he end of the day......better sound is better sound....just something I’ve thought about