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

I have listened to multiple $500K systems.  My usual reaction is ho hum.  They sound good but my "ah ha" moment is how little you need to spend to get excellent sound!  Careful matching can create great results in the $10k - $50k range.

I’ve got 3 audio systems to listen and compare, ranging from my car (Acura 2004 TL) to a Bose Computer setup and my home “Audiophile” System....around $40,000+/- and growing rapidly.

I enjoy all 3 of them, almost equally.
Music 🎶 moves me when it’s really good and well recorded so I can enjoy it regardless of the quality or the sophistication of whatever I happen to be listening on at the time.
Its the music, not the equipment we should be enjoying. 👍

Audiophiles enjoy the sound as much as music.
$10k new will not get you anywhere close to great sound even in a small room and one source. $50k new is possible in small and medium size room but tough. That said, $10k system with one source can sound pretty good in smaller room. Great means great in my vocabulary.

Strange thread topic.  Has anyone made the drop to entry level cheap made in China budget crap and been ambivalent about it?

I totally agree with Pokey 77 and bmontani.
Through the years i haved been climbing up the ladder. Had some nice equipment that i traded in, with some cash added and got a even better equipment/sound. Always tried to find the weak spot in the chain and the best gear for the money awailebel.
About 20 years ago the cabels became real components and the level raised substancial, then the decoupling and all the room treatments etcappeared. The tweaks have raised the bar so high that i often think its much better in my musicroom, than real concerts (not acoustical ones).
In the beginning i was analysing the soundstage but at a point it became much more emotional and here is is were the ultra highend stuff really makes sence to me. 
I can also lisen to a low level system but at a very low volume and not for so long time. In order to get a ultra highend system where you have a concert in front of you, there are so many things( in fact everything) you need to adress.
 Its my expirience that you never get a superb sound at a show because there are so many thing you cannot control. It takes years of hard work to reach a ultra high level and today i would say the tweaks is 50% of the result. The rest is split between the music material and the hardware.
Beleave your ears and emotions or ask your wife.
I have never regreat using a huge sum on my audio/music life but i almost only buy used gear as my budget is limited. If a component dosent perform well, try another. Nice designd and handmade gear can always sold again.
Worst deal ever: was a pair of Halcro DM 68 amps, they arent making music in my ears. I tried them and sold them quickly again but they thought me a lot about musical feeling. 
Best deal are the 2LP 45RPM's from the late 50's. 
Biggest problem, is the lack of posibillityes to try equipment before buying it. Dealers are worth giving a higher price if they give a proper service. 

Happy lisining.