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've owned my pair of Quad ESLs since 1973. They were eventually put to the side (and eventually into crates) while I used the Crosby modified 63, which was, overall, a better performing speaker in terms of bass, dynamics and dispersion, but they lacked the utter coherence of the original in my estimation. I only recently got my original pair restored by Kent McCollum, and they sound wonderful, with a pair of old Quad II amps, restored and re-glassed with GEC KT 66s. I don't have fancy wire, and in fact, have still not finished the turntable, so am using a CD player as a source-not a particularly notable one. The Quad based system is a joy to listen to.
But, there are many other things I own that I also like:
-my Lamm ML2s are wonderful with horns. I will probably not part with them.
-my Kuzma XL and Airline arm is now in its 11th year of service and I'll still thrilled with its performance. I did have to buy a pricey isolation platform for its new location, but it was worth it.
There are a number of other components I have owned over the years that I regard as enduring and bring me joy.
The point of diminishing returns is a very personal one and cannot be measured by any objective criteria in my estimation. Now that I'm past my big earning years, I'm more sensitive to value for the dollar but never felt compelled to upgrade for the sake of the latest and greatest. 
I'm finally looking at digital sources, to give me more access to music, despite my life long commitment to the LP.  
For the last number of years, most of my money relating to hi-fi has gone into records, not gear. I'm also enjoying it more than ever. 

Ok Ill bite.

I don’t think my system is super high end, compared to others on Audio Aficionado, but I’ll give you insight into some of the pieces I have. Because this thread is asking about pricing, I will include prices as well.

Speakers: BW 802D3 ($22K, paid $18K)
Source: Emm Labs DAC2x ($15K, paid $5K) + Emm Labs TSDx Transport ($15K, paid $5K)
Preamp: Cary SLP-05 tube preamp ($7.5K, paid $3.75K)
Amp: Boulder 2060 stereo ($46K, paid $17K)
Speakerwires: Audioquest WEL 8ft single/biwire ($31K, paid $5K)
Power Cords: Audioquest NRG-WEL 3ft x2 ($4K each, paid $1K each)
XLR: Still need to upgrade
Power conditioner: PS Audio P5 Regenerator ($3.5K, paid $650)

I have a dedicated and treated room, just for stereo.  I have clouds hanging from the ceilings and treatments on all 4 walls.  I have dedicated circuits for the room as well. 

Based on my experience, there are certainly certain components that actually made a difference for me. Is my system perfect? I don’t think so. Some pieces are still in flux and will likely be changed as time goes on.

2 things that will probably not be changed? The Boulder amp and the Audioquest WEL units.

Is there diminishing returns? I believe so. But I am pretty happy with the performance I got from the units.

I thought the difference going from my old Cary 306 SACD to the Emm Lab units was excellent, more real, more analog, yadda yadda... IMO, it was worth the $8K delta that I paid. Would I pay $30K for the 2 units? No.

The difference going from my previous Classe M600 delta monoblocks and the Cary 211FE tube monoblocks to the Boulder 2060 was very significant. To me, it was a no brainer coming from those $8K (used, paid) units to the $17K Boulder... the difference was very significant and was worth the delta in price again.... would I pay $46K for the Boulders? No.

The difference going from my old wire regular 12g OFC and Satori units to the AQ WEL was very significant. Definitely worth the $5K I paid... would I pay the retail of $31K? No way.

So, yes, diminishing returns are in play here, but I feel like the units I have which can be considered to be pretty high end, do display improvement over lesser units in my room and to my ears, would I pay the exhorbitant and racket pricing? No way.

But to me, for what I paid, it was worth it.

But yes, someone said it earlier in the thread... you gotta be very careful with these upper end purchases, moving them or flipping them is not easy as the market is much thinner as you move up. Some people have so much money they would rather buy new and have dealer support than save some cash and pay used.

Just my 2 cents.
The point of diminishing return is a moving target. Depends on the amount of discretionary funds available, and knowledge base acquired by the person developing the system. 

Those with a deep pocket and a shallow knowledge base are more likely to end up with an expensive system that could easily be bested by a lessor expensive one.

A large component of the knowledge base required is to understand what one's own preferences are. This takes exposure to many systems.

My discretionary funds are limited, my knowledge base not near the point of diminishing return.
Re: Law of Diminishing Returns
Just to chime in on the subject of diminishing returns, I don’t actually believe there is a Law of diminishing returns for audio, there’s no hyperbolic curve, or some artificial ceiling that cannot be surpassed. "I don't think it's worth spending twice as much to get only the last 5%." 😀 What is required is thinking outside the box. Audio is an art as much as a science.

There is also the principle of "stove piping" involved here I suspect, where audiophiles develop their systems more or less in a vacuum. And each person reaches certain conclusions based on what he finds out. Each one declares he has found Audio Nirvana, yet when an independent observer listeners to those systems he discovers that they don’t sound nearly as fabulous as their owners claim or believe. In fact, by and large, they frequently sound quite bland and generic and distorted. You know, kind of like those big expensive systems like at big audio shows.

"Wow! What a view, I never thought I’d be on the summit of Everest!"
"Calm down, were only at Base Camp. We’re only half way up."

Yer a stove piper
Stove piper, stove piper, stove piper, stove
Stove piper, stove piper, stove piper, stove