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

I like to design stuff that has exactly zero capacity to be replaced by anything in the market, today -- or tomorrow.

Notable quotes

"The Ford Model T is the last car you will ever own." - Henry Ford

"The iPhone is the last mobile device you will ever own." - Steve Jobs

"This is the last Audio Research preamp you will ever own." - whoever

"The Hubble Space Telescope is the last space telescope you’ll ever need." - NASA bigwig

"The Space Shuttle is the last reusable manned space vehicle you’ll ever need." Different NASA bigwig who was also quotes as saying, "The Space Shuttle is perfectly safe due to NASA's strict program of quality control and triple redundancy."

But Continuum turntable might in fact be the last table you'll ever need. I would get their classic Caliburn, though.

It's been fun reading some of the comments - only I think 2 people have answered the OP with actual examples (Thank you @joey_v  )
I have "ventured" into a land far higher-end that I thought. In fact...I was in the camp of what some might consider the 'curmudgeon' approach where just about anything in the high 4 digits was a virtual ripoff, and 5 digits was DEFINITELY a ripoff. I took a 'break' from the hobby for about 10-15 years (I left it with some dabbling in SET's and high efficiency single-drivers stuff. Honestly, sucked the life out of music for me, in my experience-there is a lot to consider in those types of systems.) Enter some find audiophile friends who have 5$,$$$ to $$$,$$$ invested, and well invested. What I heard brought the joy back (and, ultimately, the hobby back to me).
4 years ago, I 'jumped back in' with some used items, and a new VPI Scout. The system was a refurbed APT Holman pre, Audire Forte amp; North Creek Music System speakers (and the Scout, with a 2MRed...then went to Dyna 20X2). It sounded really good. However - I (maybe like the OP) wanted to see what this other 'place' was - and I had some extra cash, also something I never had before. So...here we go..about 2 years ago the upgrade-itis bit hard: 
Purchased gently used, over the course of 1 year: Jeff Rowland Synergy IIi, Jeff Rowland 501 mono's, VPI Aries 2 with JMW10 (two arms for Dyna 20x2 and Ortofon Quintet Mono). Silent Running Audio platform, and Tannoy Monitor Gold 12's (which I have had for years, just not used) in a custom enclosure, with crossovers by Reference Fidelity Components (UK). I have now been 'testing the waters' a bit with interconnects. I have some Cardas in the system now (Using all balanced was a revelation to me, btw.) I also installed a dedicated 6kva isolation transformer for the audio system power lines.
HERE's THE BIGGEST THING: A DEDICATED ROOM. FINALLY. :)  I haven't even begun to scratch the surface with acoustics yet, aside from speaker placement and some first reflection points. But my next big action will be a full acoustic work up, so as to get a plan together.
Was it all worth it? Yes...Did I have buyers remorse at some point? Yes: that moment when the sound changes so much (a) you wonder what you broke (b) did it get better? (c) YES IT DID! HOLY COW - my background noise got so quiet, I wasn't used to that.... wierd....
Honestly speaking, I had to re-train my ears bit from some harsh treble which I'd come to expect (and maybe even look for?) to a non-fatiguing, smooth sound that was so natural. I doubt the journey is done for me - but maybe my "near hi end" system will morph again.  We'll see.

@boneman

thanks for the mention

i will say that you are right about the room, it is the most difficult piece to attain and perfect.  My room is nowhere close but it is dedicated and I have no waf to deal with.  Maybe I can perfect the dimensions and room construct with the next house if I am so lucky.

But yes, I have a symmetric 18x15x9 room with slanted ceilings and no odd cubbies or halls.  I have the absorption down pat and just need to work on diffusion.

The experience in my main room is far more of an "event" than any of my 2 lesser systems.  The Sonus Faber Olympica 3 system in my family room is a pale facsimile in comparison.