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

During the past year I have upgraded both my headphone system and my main speaker system. The total price for the headphone rig (dac, amp, headphones was <$1000 and the sound is incredible. I think the law of diminishing returns would kick in big time beyond that price point. The same could be said about my main system <$5000.

OK, time for me to fess up. Someone asked a little while ago if anyone went the opposite direction from upgrading to a super high end system. Guilty as charged.

Two years ago I had a rather good but not terribly expensive headphone system with pure tube Woo Audio headphone Amp with all NOS Tung Sol and Sylvania tubes, a VERY modded Oppo DC player, including the Linear Power Supply mod, Analysis Plus ICs and Power Cord and Nordost Blue Heaven power cord. Oh, two count em Herbies tube dampers per tube for total of 6. I used cryo’d, naked Sennheiswr 600s with Stephan Arts cabling with that system.

Since then, just for experimentation, I went to a much simpler system based around a Sony Walkman portable CD player and Sony Walkman cassette player with Grado SR-60 headphones. I have no power cords, no interconnects and no speaker cables. I also have no power transformers, no grounding issues (since I dint have a ground), no fuses, no house AC, no big honking capacitors, no digital cable. I already got out of ye olde room acoustics game with the last system. No more teacher’s dirty looks. 😜

Interesting thread.  I will weigh in (but with massive caveats in the TL;DR section)

- My end is low high-end compared to one with a $50K amps (I surmise a $50K amp probably means $100-$200k or greater systems).  I.e. my end in $ is just a bit more than that of a $50K+ amp in total.

Before shooting arrows at me, please read the TL;DR section after the regret/non-regrets - OK - hopefully that makes sense.

Regrets: 
(1) I regret experimenting with ~ $10K of digital amps except my modded NuPrime st-10 (home office use only).  They are cool (temp wise and tech wise), but my tube and SS amp are better suited to my ears and system.  Fortunately, they resold OK.
(2) I regret not getting a tube amp sooner - its not a panacea, and for some music I do goto my very fine sounding SS amp.  But for a lot of my vinyl classical music - its the thing...
(3) I regret holding on to my prior gen speakers and not getting them mfg upgraded sooner.  they are quite amazing now.  And for TVM - a great value.  
(4) I regret a slew of cheaper phono cartridges before I found a relatively expensive, well regarded, high-end cartridge (ZYX Universe II) wow.  Made a bigger difference than my $10K table over the prior $3k table.

On the fence:
- Power conditioning.  Most of the benefit came from careful power grounding (see #4 below).  I have not noticed any change in musical parameters - although I tend to feel its a bit cleaner / tighter sound all around - but hardly...

To be balanced, a couple of non-regrets:
(1) Went with well regarded modest cables - mild change to overall system, not worth the $ but happy not to have spent $$$$.  I did put in one set of $$ cables - it was meh.  At least for me, cables do change things around a bit in what I hear (I'm sure there are theories re: signal noise due to grain boundaries, magic impedance matching, cold-fusion-electrons and so on).  However, the value for cable $ going to $$$$ has been better spent elsewhere - if not just for having more $ for music itself (i.e. real-record cleaning machine, vinyl and HDtracks...)
(2) Tube pre - VTL is great
(3) Having both a tube and SS amp.  I found one of each type I can listen all day to.  And yes, my tube has a bit more neutrality than some tube, and my SS has a bit more sweetness than some SS.  The SS rocks better - but works for all.  The tube is for vinyl classical music - but works for all.
(4) Having spent about a day working out the safe and correct grounding scheme between all equipment down to their power sources - keeping to a "star" as much as possible for the power, and carefully checking which equipment induces noise/hum - and checking the condition of the grounding and so on.  I have no "removed" pins, no unsafe grounds and so on.  I have no hum nor noise from mains or induced either...

TL;DR Section:

The long-list of caveats:
- I've dealt with $800 up to my current system intimately
- I've heard up to $100k+ systems, but not in a home - only at a high-end dealer (and more than one didn't seem right to me - probably their setup, but certainly dissuaded me from some massive purchase)
- I've always had a mental "guide" for myself (please - this is only my rule, not a recommendation to anyone) I want to keep my audiophile equipment urge to something like low-single-digits % of net-worth - not much more. The one time I broke that was when I was in my late 20's and bought speakers well above my pay-grade - and kept them for 20 years.
- Another mental guide - if I bought a single component (aka speaker, amp) I had to promise myself that for the $ I spent, I might be mad, but I could not be really-sad if I lost that $ to a disaster. I.e. no risking a house payment, kids college fund and so on if I lost that $.
- I don't sell the last component till I'm OK with the new. In reality, I still have more than 50% of my last 2 generations of components. And I had my last generation speaker upgraded by the Mfg - and it now sounds great in a our cabin in the woods.
- I don't feel I have golden ears. I have played in orchestras, still play piano, like a mix from classical to rock, notice the difference from vinyl from digital (and not just the noise aspect), notice the difference of a tube chain vs a SS chain (actual system experience), sometimes notice the difference phase-inversion can make for some recordings
- Still get fooled by a change-sometimes-sounds-better-initially syndrome. Only to realize after a few weeks of listening that going back to the old setup "sounds better" again (and later change again to sound better :). This is mostly from power and signal cable changes.
- I have had people listen to the system who have much much better systems and heard much much more equipment. They tend to say "sounds good", "you could improve a few things, but for the money pretty good". We tend to find the system is: Not as "big" dynamically as the best. Very good on vocals, but not the bees knees on "in your face" projection. Good bass floor, tuneful bass but not a room shaker. Stage is about 1 foot wider than the outside of the speakers (set about 9 ft apart, sitting about 9 ft away) - good not great. Spatial resolution is in the 1-2 cm range, not millimeters (again good, not great). Very even tempered up and down the frequency range - I'd say its one area this system is excellent at, and favors my ears and listening preferences. Not razor edgy, not blurred - not super sweet, but not super airy - not as tight as a steel wire, but not bloated - Good balance for these attributes.

FYI:  System inventory today (about 75% are used purchases which kept $ spent much lower than retail):
- Revel Ultima Salon 2
- VTL 7.5 mk ii using psvane 12AU7 (did some NOS and modern comparisons, and have about 12 pairs of different 12AU7 in my collection - some are meh, some I'm saving ...)
- Ayre DPS turntable
- Ayre P-5xe phono preamp
- ZYX Universe II cartridge
- NAD M50/M52 music server and DAC
- Wells Audio Innamorata SS amp [PS:  This is a very very very fine SS amp - not crazy expensive.  I had someone unsell me from a $20K amp to look at this one.  I bought straight from Jeff Wells the owner.  If you are looking to spend ~$7K on an SS amp that kicks way above its $, this is it.)
- Primaluna HP power amp (KT150 tubes) - people say this is lush with the EL34 (I have a set) - but in my system and room, this works out the best balance of tone, dynamics, prat and all that
- Analysis plus through out the system except:  JPS superconductor from pre to tube amp
- An odd mix of power supply.  We have voltage sags due to "power days" so I do have my outlet "fronted" by a APC HT15.  It feeds an Audience AR6.  That feeds all the equipment with the help of a Shunyata power distribution strip (no NR, just nice a shiny looking).  Current heavy devices straight to AR6.  Light current devices into the power strip.
- Hannl record cleaning machine (old style)

I listen to what I like regardless of the recording quality, and in most cases it is not good to various degree. Yet, even the worst of them sound a little better with each small upgrade. At the same time you hear better recordings’ flaws as well. As for the tailoring your system, especially speakers, to the kind of music you mostly listen to, in reality I think you have to unless perhaps it is an absolute super high end, whatever it is. Though I listen to some jazzrock, mostly it’s various acoustic music including vocal. For rock I would choose very different speakers, Pink Floyd plays okay, though.
I also think that no super high end set-up can be called that without top open reel deck as a source, in addition to turntable. 

For most of us, I think it may take a good 2 or 3 decades of familiarizing yourself with the market in this hobby to get to a reliably good enough level of experience with which you can feel good about your chances of success at downsizing and getting away with it. It takes that long for most of us to become familiar with the width and depth of the market and it may not come at all unless you’ve made a number of purchases, for both good And ill, and have lived with the results for a long enough while.

But, just remember: having gone down the slippery slope, every time some audiophile proclaims their rallying cry in print that the paying of the exorbitant prices is ’unquestionably’ the only way to go, there’s another manufacturer that says to themselves: "See that? More proof that if I introduce a new product to the market at a temptingly competitive price that I know I can still make a profit at, then I know it won’t be taken seriously by anyone unless I price it 2-4 time higher". This is how the industry is pricing itself out of existence.

Of course, the original problem was created by the makers, pressuring us whenever possible in subtle and in not-so-subtle ways to spend more than last time. But, it’s a runaway train and about everybody is at fault.
I would suppose the only sane thing to do for both our own And the hobby’s sake Is to learn how to downsize from the top...or maybe better yet, to finally put in the time it takes to learn how to never actually go down the all-out-assault path to begin with - or at least not without extreme care - surely a tricky and time-consuming thing, particularly if you’ve ruled out all expensive purchases from the start.

OK everybody, now relax and just enjoy the music...if you still can. :(