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.

@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. 

from a thread, on another forum... on damping materials - a post I made today:

What it comes down to (took many years to zero in on the true issues at hand) is that a interestingly high number of designers and most electronics people have zero (or near zero) information on how the ear actually works, and how this correlates to electronics.

Doing it right, requires that a quite wide swath of data be understood and brought to bear on the problem. Then to design and build along those lines. and then..get it out to the public.

....At which point, one would just be seen as another prophet screaming on a stage among a thousand other prophets screaming on their stages, all in the same room. Truth or correctness in these areas has but one voice in a room of a thousand voices.

Pretty darned difficult to see it, is the end result.

The fact that each person has different results in a scenario that should be uniformly clear, brings this point home, quite effectively. That is, if people look at the whole scenario with enough clarity in thought. There is an order to this thing, this issue... this industry wide fundamental issue, but it can be difficult to see.

~~~~~~~~~

Basically, we’ve become so inured to the complexity, the sheer Gordian knot-like characteristics of the issues... that we’ve settled on the idea that the differences are the norm and nothing is really truly correct. When in fact, this is not true. I detest anything factualized and thus dogmatized (as both create and maintian circular dead ends), but there is a way out- a more corrected path in this audio issue.

I did propose the basics of a path out of this particular dark woods and I did it in what is essentially a room full of audio designers. The blowtorch thread on DIYaudio.

I’ve been waiting for a few years to see if it bears fruit.

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.

Oh, well, I guess that's the way the cookie crumbles. 🍪 No offense.