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

TOO MANY variables influence sound production. However to me the most important involve the original source material (CD Vinyl DVD etc), understanding your room acoustics, the quality of your speakers (they are the main transducers after all, spend your money here). Good ones are easy to pick out. Also a good amp and preamp. I say good because
amps long ago reached the "start of the art". However it should match your speakers well and you should LIKE the sound.  Finally if you are into vinyl a decent turntable and especially a first rate cartridge are big factors in how well vinyl will sound.  
 You really need to play around with speaker placement to get the best sound in a given room. Acoustical engineers will always tell you that in setting up a theater sound analysis is paramount.

Personally I think that an excellent system can be had for far less than the super high end and that the law of diminishing returns
sets in fast after you spend $30,000 for speakers, amp/preamp and
input devices. 

One last thing, if you have poor cables or your power is of questionable quality you will never be happy in my opinion.

Finally, many of us are a bit obsessive and consequently are never
quite happy with our systems. That's OK but the industry counts
on that personalty trait to sell the next big thing. So most of all just ENJOY THE MUSIC.

It’s true that there are a lot of variables. But variables CAN be controlled. Time of day, day of week, the weather ⛈ sunspot activity 🌞 humidity, whatever. You change ONLY ONE VARIABLE AT A TIME. Then you will know what causes the change - the one variable you changed. Hel-loo! It ain’t necessarily easy. Nobody promised you a rose garden. People climb Everest all the time. 🏔 Even though it’s not easy. Audiophiles don't even know what ALL the variables even are, for crying out loud. 😫  In order to progress you kind of have to know WHERE you are and WHERE you want to go. AND how to get there. That really is the key. 🗝 Otherwise, you’re just shooting blanks in the dark. 🔫

People don’t really seem to know where they are on the overall curve of performance or what is really possible. I know what you’re thinking: "but what about live unamplified sound?" As far as knowing where to go next they’re apparently pretty much stuck between a rock and a hard place. As I posted earlier everyone is stove piping. 🏭 Everyone reaches different conclusions. Stove piping, stove piping, stove piping, stove! Yeah!

What @geoffkait  calls "stove piping" I, and others, call trusting our ears. It's worth a try.

People with the means to afford living voice vox olympian speakers and comparable gear also have the means to discard such electronics (as a tax write off, of course) and simply buy whatever else is on their mind at any particular time. Also, not likely they contribute in writing or reading to audiogon forum posts.

jond wrote,

"What @geoffkait calls "stove piping" I, and others, call trusting our ears."

Whoa! Hey, it's not nice to put words in someone's mouth. Stove piping means nothing of the sort. Stove piping is an Intel expression that refers to the problem that arises when multiple organizations and multiple individuals/sources come to different and contradictory conclusions regarding political situations, military actions required, probable actions/motives of individuals or states, etc. Stove piping is an undesirable situation that arises because of lack of coordination and lack of oversight. This is what happens in the audio hobby, too. It's very disorganized. It then becomes a game of, who do you believe? Follow?