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

We can go on forever about it, can't we ? 

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 That tech goes out of date so fast, and seems like it is really off-the-shelf.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.