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

My current rig is total value of around $50K.
My first real high end system was around $5K.

I can honestly say that all components I have upgraded over the past 12 years until now have been improvements over their previous versions.  This includes speakers, amp, preamp and turntable.

Of these upgrades the ones that had this biggest impact were speakers, turntable and phono preamp, in that order.  

For now I am sticking with what I have, as I am very happy with its performance.  I do get curious about other gear quite often, but when I consider the cost to go up the line I decide it's not worth it (at least where I am at right now).

I cannot imagine ever owning a system that eclipses $100K, but I do dream about it.  I think at that point it becomes more about status than about dramatic improvement.  A lot of people care just as much about what their gear looks like as the performance.  My guess is my system gives me 90% of what a $250K system would, but it definitely doesn't look as cool or exotic. Ultra high end is sexy stuff.  I get why it is so attractive to so many.  The feeling it gives you when you look at it is definitely a big part of the equation.
 

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 That tech goes out of date so fast, and seems like it is really off-the-shelf.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