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

I think one thing that plays a key role (no matter what audio $$ level) is each new addition (or improvement) may highlight some other weakness that did not stand out before. Even if very minor. That is where "tweaking" with things like cables, room treatments, power cords, etc may come in. I purchased my new Nuforce amp a couple months ago. The bass and the clarity was there. However, just a smidge harsh on upper frequencies. I purchased a new tube Pre amp and the harshness is gone and I have silky smooth mids. I was not expecting, when I purchased the Nuforce amp, to pay an additional $3500 for a tube pre. It's a constant give and take

That’s because you have to get the entire set-up at the same time and then leave it alone until you are ready to go to an even higher level, instead of endlessly tinkering with it.
Yes, difficult and very expensive. But we are talking super high end.
We are obsessed with gear audiophiles because we are poor and lazy.

For 45 years as an Audiophile I'd buy a piece, tweak, change, replace, and repeat.  I DID have a period of about 15 years where I didn't change a thing, just sat back and enjoyed the music.
Then, to get to the OPS question: I literally "hocked the house."  Went to a shop picked out speakers, a matching amp, pre-amp, turntable, cartridge, DAC/CD player, and miscellaneous interconnects/cables.  In all the system cost nearly 10X my old system.
Now nearly 2 years later, system is getting a bit boring / taken-for-granted.  Do I wish I didn't hock-the-house, or bought a few new cars instead yeah sometimes..........

I wonder why someone hasn't repeated the long overdue motto that should hopefully end all the high-end bashing: "You can hear everything you can measure but you can't measure everything you hear". 
Good quality speakers are important but so is every part of the chain. Amps are incredibly important. Pre-amps are the absolute heart of a system. High quality source material is fundamental to great sound. And all the cabling is imperative to making it all work together. Finally, the room is absolutely instrumental in allowing it all to work. Good sound is not hard to find at reasonable prices. Very good sound can start to get pricey. Exceptional, almost soul stirring and truly transformational sound takes a tremendous amount of dedicated time, a lot of money, usually a dedicated listening room and even a lot of pure luck... but when that all comes together ideally it is SO MUCH BETTER than anything less than a live performance, there simply is NO comparison. It is a spellbinding experience that truly quenches an inner thirst you never realized was so parched.
As much as I'd like to say that "Plenty good enough" purchased via " good value" sounding equipment is all most people need... all I can say is "What you don't know you're missing.. you won't miss". But for those fortunate enough to successfully get through all of the above hoops/hurdles and contortions, 
music played through such a system will be the tall cool glass of your favorite beverage at the end of your daily jaunt in the desert. And well worth ALL the work. Happy Lissn'n

Agreed. It is worth it if you are up to what is involved. And the cost will be very high, it has to be.