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

I'm talking $50,000 and higher amps, speakers, cablesetc. I know there is excellent sounding gear from $100 to infinity (much is system dependent, room, etc). However, just curious if someone made the leap and deep down realize the "expected" sound quality jump was not as much as the price jump. Unfortunately, I'm not in a position to make that jump. However, looking at another forum's thread about price point of diminishing returns got me wondering if anyone had buyers remorse. It's not easy to just "flip" a super high priced component. 
I found that it's much easier to build a satisfying $25k system or even a $100k system.  Those systems necessarily have the lower resolution that covers up a lot of faults in the recordings and the systems. 

I wasn't really ready for the jump to the lower stratosphere where every component change revealed a flaw/weakness in my system that necessitated another commensurate component change.  For example, earlier this year, I unexpectedly was "forced" to upgrade my front end since I love CDs and EMM said that it was likely their last spinner, which revealed my speakers lack of clarity and further reinforced the fact that their top end was exceedingly bright.  So I decided to upgrade the speakers which confirmed my beliefs about my previous speakers but revealed that not only were my 300W monoblocs insufficient to properly drive my speakers (never thought I would say that) but more importantly made even clearer a whitish tinge in the treble.  I figured that was just part of high resolution until I was auditioning a set of replacement amps that can properly drive my speakers (and pretty much any speaker I can think of) and shockingly it went away (which was a bonus - there were many other factors that made me bite the very expensive bullet on the amps).  So, waiting on the new amps and crossing my fingers that I'll be where I need to be since the discretionary budget is tapped.
Although not as expensive, upgrading recordings can add quite a bit of cost. With each new remaster, hi rez release, im sure many own multiple copies of a single album, in many formats. Myself, I have pretty much purchased every vinyl, cd edition of Dark Side of the Moon thru the years. 
Come on fellas, if you spent 50 grand on a stereo system and we're not happy, would YOU admit it?
Think about it.
Whoever out there does is the God of Honesty and don't think there is one.

Sitting here banging out some Hank Mobley, "Uh Huh" through the Quad 989s, Wolcott amp and Lamm pre.
Life is good.
Great thread.
Come on fellas, if you spent 50 grand on a stereo system and we're not happy, would YOU admit it?

Fifty grand isn't even close to the expenditure needed for a $uper high end stereo system.  :)
The $1 Million super system at CES 2001, which I’m pretty sure was comprised of monster Wisdom Audio speakers and a bunch of huge Plinius amplifiers sitting on a stage of the appropriate proportions, sounded, well, not..too..good. I hate to judge before all the facts are in, but I’m pretty sure throwing money, even massive amounts of it, at the problem is not the answer. I was supposed to go listen to the Million Dollar System, which had generated considerable buzz that day 🐝 with a couple of guys but I made the mistake of sticking around at two big rooms I was supporting hoping for a miracle.

Which reminds me. In the 80s they had a CES in Washington DC area and I attended a big demo of the Audio Research electronics driving the monster Infinity Reference speakers, the ones with the outboard stack of woofers for each channel. The source was a big reel to reel. The dude conducting the demo stood on the stage and alerted the audience that they were about to hear sound that was indistinguishable from live music. I cannot recall what the recording was they played but as soon as it came on everyone looked around at each other, incredulous, and raced for the EXIT doors, your humble scribe included. 🏃 🏃 🏃

"A rich man has about as much chance of attaining Audio Nirvana as a camel has of passing through the eye of a needle." - old audiophile axiom