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

Well, there would be a lot of frustration on the way. In that sentence I meant money, though.

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.
GJI

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.  :)