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

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.

Have to agree with Stingreen.  Depends on what you want to hear your system reproduce.

Terry9 - why use a resistor volume control at all?  Try a transformer volume control as all resistors have a sound.

My preamp has no capacitors in the signal path with a TVC and DHT tubes.  Sounds amazing.

Now go build a pair of field coil speakers and see what happens!

Happy listening.

I have listened to multiple $500K systems.  My usual reaction is ho hum.  They sound good but my "ah ha" moment is how little you need to spend to get excellent sound!  Careful matching can create great results in the $10k - $50k range.

I’ve got 3 audio systems to listen and compare, ranging from my car (Acura 2004 TL) to a Bose Computer setup and my home “Audiophile” System....around $40,000+/- and growing rapidly.

I enjoy all 3 of them, almost equally.
Music 🎶 moves me when it’s really good and well recorded so I can enjoy it regardless of the quality or the sophistication of whatever I happen to be listening on at the time.
Its the music, not the equipment we should be enjoying. 👍