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

Good thread, hard to add much to the very good views presented.  But here's a question that over 39 years of system building still baffles me.  That is what seems to me the impossibility of building a system the way it should be built, i.e. by auditioning any significant purchase in your own system.  You can go to shows, read reviews, and other research, but it is just not practicable to home audition most gear (yes, The Cable Company is an exception).  So what happens, at least to me, is that you need to meet a dealer you can trust.  And even if he is willing to allow home auditions, your choices are still limited to the brands he carries.  You can still do well this way in building the system, but have to admit you have no idea how it sounds compared to the great variety of good equipment out there.  The point being that in building a system, one's knowledge base is necessarily limited.  And I want to Listen, not work (while admiring those who do want to work).

Not to mention the forest of directly conflicting claims by numerous respected professionals in the field, most of whom presumably are people of integrity who just have differing views, but nonetheless they provide little reliable ground to stand on.

As for the original question, rephrased, "have your high end system purchases remained worth it?", my general response is that, even though I consider myself a value shopper always very mindful of diminishing returns, and am in fact very happy with my system, I have seldom gotten the level of sound quality I expected from any major purchase.  Maybe inflated expectations.  I agree with those who have cited small tweaks as often exponentially more cost effective than major component changes.  And I agree with the many comments about good sound from modestly priced systems, having owned my fair share (how about Infinity 3000 speakers, or any Rogue or NAD product).

But to emphasize, the above statement does not contain an implication that I don't enjoy my system--it sounds beautiful, I am glad I've spent the coin and feel I've gotten good value (while acknowledging there may be very different opinions of that).  System is Aesthetix Eclipse stereo amp and preamp, Resolution Audio 3.0 CD/DAC, Antipodes DX digital front end (no vinyl, tape or 'phones), Vandersteen Model Seven MkII speakers, and medium-high end Audioquest wires, old RGPC power conditioning with amps plugged into wall, Mapleshade rack with 4" shelves.  Maybe new retail total somewhere around $130k (yes, a ridiculous amount of money), I bought majority used or at good discount.  Again, despite liking my system very much, I would have thought this level of expenditure would provide better sound, mindblowing sound, actually.  Again, maybe unrealistic expectations.  But that consideration doesn't matter.  What does matter is that I enjoy the system and am glad I've bought it.

As you can gather, my response to the original question is that I am delighted at what I've gotten for my money, and disappointed at what I've gotten for my money...

I also agree with a previous post who suggested it takes a lot of time and effort to put together an agreeable system, and with another who said that very good sound is unavoidably expensive.

And now, with the mercifully increased dark enabled by the end of DST, I am about to turn on the system and enjoy the beautiful music.
jimski

My current rig is total value of around $50K.
My first real high end system was around $5K.

I can honestly say that all components I have upgraded over the past 12 years until now have been improvements over their previous versions.  This includes speakers, amp, preamp and turntable.

Of these upgrades the ones that had this biggest impact were speakers, turntable and phono preamp, in that order.  

For now I am sticking with what I have, as I am very happy with its performance.  I do get curious about other gear quite often, but when I consider the cost to go up the line I decide it's not worth it (at least where I am at right now).

I cannot imagine ever owning a system that eclipses $100K, but I do dream about it.  I think at that point it becomes more about status than about dramatic improvement.  A lot of people care just as much about what their gear looks like as the performance.  My guess is my system gives me 90% of what a $250K system would, but it definitely doesn't look as cool or exotic. Ultra high end is sexy stuff.  I get why it is so attractive to so many.  The feeling it gives you when you look at it is definitely a big part of the equation.
 

We can go on forever about it, can't we ? 

Read whitecamaross’ thread, " My Long List of Amplifiers and My Personal Review of Each!"

He swaps expensive gear like the rest of us change clothes and has his mind blown by his new gear on a regular basis. His cost is on a generally, but not always, upward trend.

I think part of his frequent amazement is the new factor. What sounds amazing to us at first often becomes only ok after we’ve gotten used to it. I think for most of us the way to go is to have a system we like, but is not the ultimate, and a Tidal subscription, and get our kicks discovering new music instead of buying new gear. On Tidal I listen to a lot of music I would never buy and find a lot of stuff that I enjoy.  Maybe not forever, but it's definitely good for a few listens.

I think the only thing I would regret paying for, if I had unlimited money, and spent it on audio equipment, would be music servers. I cannot conceive of a way for a computer system with ethernet and USB to cost over $10,000. Probably not over $5000. That tech goes out of date so fast, and seems like it is really off-the-shelf. I don’t believe the people selling it have the know-how or the technology to justify the price. They don’t have the skill to produce systems that can cost that much. But I don’t have the money, so I just don’t know. Everything else, I would imagine is a joy to own. And I don’t imagine anyone that owns it would say otherwise. I wish I did.  My current everything, with tubes and cables is over 10k so I'm a guppy in a big ocean.  But I’m also an IT professional, so I know computers and data transfer.