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

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.

I gave the OP a bit more thought, and reflected on what I wrote a 'few' posts back - - the original question, summarized, was "have you been disappointed by the high end" - or another way to read it is 'was the dollars worth it'. So...buried in my life history post, a few back, I mentioned a journey into low-power, high efficiency. This was in late 90's ('98-'99). That was no where near high-end $$$$$, but it did cost me some money. It sucked. I tried - and it was like a carrot-on-a-stick and I was the camel. Bass was problematic in my room, mids got over powering. I never found a horn that (I could afford) I liked - and Fostex drivers were OK, but lets revist that bass issue. Oh - lets roll some tubes now. It's an interconnect thing. Ugh. Maybe I'm not putting enough money into it (but my pocketbook is bleeding - oh, maybe I have no business even trying this if my pocketbook isn't deep enough). Hah.  So - was that venture worth it? Nope.