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

@jond 

Yep, "believe yourself. And your ears." After all, you are the one who will  pay your hard-earned $$ for that high end rig. And of course you'll be the one listening to it so you might as well buy something you really like. 

I don't know if what I have is super high end, I have about 75k in my system but I have to say for me it is worth every penny.  I am very happy with the sound.  Most of my equipment is used from Audiogon and US Audiomart so if you purchased it at full retail it would probably be worth closer to 125K to 150K but no regrets.  It sounds just amazing.  Like many of the people who responded, there are diminishing returns.  To get an incremental improvement it might cost significantly more but if you have the scratch and love the hobby, it is worth it in my opinion.

@whatjd 

Please explain.

Randy-11, I did just that but did you know that granite attracts lightning? 
I would disagree that Quads and Harbeth are the best $$ can buy. I would also disagree that the loudspeaker is the most expensive piece of equipment you purchase. Quads are really nice but far from the best IMO.
you need to look at the total synergy of the system. Not all cheap amps, even with the so-called vendor specs, are equal to more expensive amps with the same ratings. I have had Yamaha and onkyo ht amps putting out 140 watts and using my older Totem mani 2’s that needed power, an equivalent Classe or McIntosh amp blew away the sound of the Yamaha or Onkyo.
say you have $20k for a complete system, how much would you spend on speakers when you know you will have to buy an amp, preamp, phono preamp, turntable, tonearm, cartridge, external dad, streamer/cdp, and cables to hook everything up. That $20k doesn’t go very far. 
You can buy the best speakers, but if you compromise on the amp (not enough power for example), or compromise on the tt setup or dac, then the best sound quality you will get is from your weakest link.

Yes, trust your ears and have a common sense. But also, especially when considering a big upgrade, try to get another pair of good ears.
That person might have different preferences so it may complicate the audition but in the end would probably help more than not.
My friend musician prefers electrostatic sound, I don’t. We can argue but what we hear is very close, only his hearing is better. But I am no punk b-tch either.