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

Above a certain level which varies from person to person, the differences become mostly a matter of taste as opposed to the actual sound quality. I know I am far from reaching that point since I can still tell when I hear a system that sounds much better than mine. And by better I don't mean just different, I mean I hear more of the music content that was absent in my home system. I think that's part of the fun of being in the audio hobby, you always look for something that makes the music more pleasurable to listen. Of course price plays a key role but for me its the incremental improvements that are most satisfying. For example, I changed a couple of the tubes in my moderately priced preamp last week and the $40 purchase was incredibly satisfying.

Nothing improves a system more than well recorded content. It could be a $500 system or 6 figures. Especially nowadays when proper recording studios are used less and less ( im talking mostly rock/pop) many expect that the $7000 cable will bring sonic bliss with recordings recorded with sm57’s in an apartment or house using protools. Also, many expect a crappy sounding hit album will somehow sound less crappy with mqa or dsd ( not taking a total remix into account).

That’s why I like Zu’s attitude at gear shows. ZU is generally cranking out fun music from all over without focusing on the “audiophile” aspect.

So, as I upgrade, my focus is on the “enjoyment” aspect of the components. Not so much on the scientific part ( although i do understand that matching components is critical).

The main reason I love my new Nuforce amp (it was ordered an in between amp...but loved it so much i decided to kerp it around longer) is it makes me want to listen and it makes listening fun. 

@aberyclark I could just as well say "nothing will bring out the virtues of badly recorded content as much as a great system"

One of the benefits of the sorts of improvements I was talking about is hearing the qualities of recordings you'd previously dismissed -- I discussed this point at length in a recent thread on considering a high end turntable investment

No, $7000 cable will not bring sonic bliss, $10k and more has a slight chance.

Two comments:
I went to my first audio show last year, the Cap Audio Fest, at one point I turned to my friend and said I was being totally influenced by my reaction to the music being played, liking the rooms where I liked the music. So absolutely recordings make a big difference.

If you are really spending $50k on individual components then I really hope you are working with a very good honest dealer. One that will give good advice and let you audition gear at home as well as ancillaries. To me that is a good way to build a system and avoid buyers remorse, at any price point.