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

Well said willemj! I agree entirely with your comments, I am sure there are a lot of people who do not. It will be interesting to hear from the folks who buy high end (read, ridiculously expensive) cables, power conditioners and similar tweaks. However, each to their own, whatever makes you happy.

No regrets. 90% of my expense is the speakers. I agree that even entry level electronics is quite good. My setup sounds great with a mere iPhone plugged in.

As far as speakers, mine are most alike to Quad but with rock and roll dynamics. Designed with the Quad in mind or as a reference.

Harbeth are really nice in the mids too (one of my favourite mid ranges) but they don't quite hang together at high levels and the thin walled cabinets tend to have some resonances in the lower frequencies.

The crux of the matter will be if they are willing to submit their casual observations to the rigours of scientific methodology. I do not doubt that they genuinely believe that they hear the differences that they hear. The question is whether they can make this stick under controlled conditions. I once did submit myself to such a test, believing I would be able to distinguish between some quality but not exotic amplifiers. Just like everybody else, I could not. There have been many such tests, and they all produced the same result. It is a sobering thought, but also a cheerful one: good quality audio is affordable for many. Socially and culturally we can only rejoice in that.
The only expensive component is the speakers, and the reason is not hard to fathom: they operate on the interface between the electrical and the mechanical, and that is far more complex than designing a straight wire with gain. Just look at the measurements for distortion and frequency response and compare those with the same measurements for electronics.
Moreover, even good speakers have to play in imperfect rooms. So compare their response in an anechoic chamber or the open air, with their in room response, and you can see that you have your job cut out.

Art Dudley discusses this same subject in his "Listening" article in the latest STEREOPHILE issue I received yesterday. Check it out.

I just read a post on another forum, "Jeff's Getting a New Stereo". The Jeff is Jeffrey Fritz Editor-in-Chief of SoundStage. After several years he's looking to downgrade from a seriously expensive system. Don't get me wrong, by any standards he's still considering expensive components. The fact that he's concluded that the ultra expensive system isn't worth it, sure makes me think!