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

Is a waist of funds kinda like a money belt?

Of course there is a curve of diminishing returns. With respect to high fidelity, it is asymptotic to the recording being played. I learned a long time ago that, for me, sound quality doesn't get better and better and better, no matter how much money is spent. Not that I would necessarily be disappointed with a much more expensive system. I'd expect a little more air than mine, and more bass definition and extension. I'd also expect it to play a lot louder. But while the ($200K?) system in the Rockport/Boulder room at RMAF 2016 sounded wonderful, it didn't sound any better than mine, to my silver ears at least. YMMV.

With respect to FIDELITY, there certainly IS a glass ceiling, and it is the recording. One may be able to improve the sound of a recording, to make it sound better than it really is, but it is logically impossible to be more faithful to a recording than the recording itself. Thus, with respect to FIDELITY, mind you, the asymptote metaphor is undeniable.

I agree that there is much more to achieving good SQ than spending more money, on "better" equipment. I just don't think SQ can keep getting better and better, without limit.