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

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.

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..........