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

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.

$50k would not be enough for speakers and monoblocks, not sure about turntable, maybe.

spend big money on a new listening room or new house

build it on top of a big block of granite too

I like Randy's idea.   Put on top of 1/2 dome in Yosemite.  Now that, would be the ultimate high end. 
-John

It takes years to fine tune a high end system.   You don't just open the boxes, hook them together and think you've got it...you don't