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

I wonder why someone hasn't repeated the long overdue motto that should hopefully end all the high-end bashing: "You can hear everything you can measure but you can't measure everything you hear". 
Good quality speakers are important but so is every part of the chain. Amps are incredibly important. Pre-amps are the absolute heart of a system. High quality source material is fundamental to great sound. And all the cabling is imperative to making it all work together. Finally, the room is absolutely instrumental in allowing it all to work. Good sound is not hard to find at reasonable prices. Very good sound can start to get pricey. Exceptional, almost soul stirring and truly transformational sound takes a tremendous amount of dedicated time, a lot of money, usually a dedicated listening room and even a lot of pure luck... but when that all comes together ideally it is SO MUCH BETTER than anything less than a live performance, there simply is NO comparison. It is a spellbinding experience that truly quenches an inner thirst you never realized was so parched.
As much as I'd like to say that "Plenty good enough" purchased via " good value" sounding equipment is all most people need... all I can say is "What you don't know you're missing.. you won't miss". But for those fortunate enough to successfully get through all of the above hoops/hurdles and contortions, 
music played through such a system will be the tall cool glass of your favorite beverage at the end of your daily jaunt in the desert. And well worth ALL the work. Happy Lissn'n

Agreed. It is worth it if you are up to what is involved. And the cost will be very high, it has to be.

inna
It is worth it if you are up to what is involved. And the cost will be very high, it has to be.

One assumes you’re referring to psychological costs. 😄

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.