I’ll have to come at this question in reverse.
When I discovered High End equipment in 1985, I started out with an AR turntable and Spica speakers. Jumped from Spicas to Apogees. Jumped from Apogees to WATTs. In the space of 1985 to 1988, I jumped all the way: Versa Dynamics 2.0 ($15,000 in 1988 dollars) Jadis preamp and amps (and Convergent preamps). Cartridges? Only remember starting at the Carnegie One and ending up with a Clearaudio Accurate. MIT and Transparent cabling, top of the line at that time. $10,000 in ASC Tube Traps alone. Was I elated? Not as much as I expected - but I didn’t know it at the time, because it still sounded (to my ears) - GREAT. Oh, I forgot: at one point, I had 5 speaker systems at once, including Avalons, WATTS, Infinity and Goldmund speakers. VAC mono blocks. The works. $80,000 in 1988 dollars. $166,000 (according to the inflation converter I just used) in 2017 dollars.
NOW, I have a system barely $10,000 total. And I LISTEN to the music. NOT the EQUIPMENT. And I am FAR more content, and enjoy the music far more.
What have I discovered over time about audio? It is that extremely important factors are: the ROOM, the electricity and isolation devices. But especially the ROOM. Still: the biggest one? MY KNOWLEDGE AND ability to set up a system completely CORRECTLY. And I was not alone in only getting maybe 80% of what a well put-together system should deliver. I once improved a system back in 1994, a system consisting of Rockport/ Clearaudio Goldfinger/Jadis JP-80/Wilson Grand Slamms/Transparent components, by doing something exceedingly simple: I moved the power cord that was sitting right on top of the speaker cable OFF of it - putting the speaker cable on a book stood up vertically, thereby removing it from the vicinity of the power cord by maybe 8". We replayed the cut and the people in the room were astonished at the improvement, and "the people" in the room were 1) the Executive Editor of TAS, one of TAS’ most famous reviewers, an amp manufacturer whose amp started with the name "BEL"...oops, the cat’s out of the bag. These people should have known that power cords should never be near, much less, on top of, speaker cables. But they didn’t. And ironically, it was TAS’ Enid Lumley who, in one of her columns, warned readers about keeping cables at 90 degree angles to each other/power cords. The famous reviewer said to me, "showoff" and we laughed together. I told him it was Enid’s column and he should be reading the magazine more carefully (he laughed).
So, it’s not the "law of diminishing returns" all too often: it’s one’s own ability to get the best out of the "super expensive system." As I usually do, I’ll mention HP, and his frequent admonishments that "setup is CRITICAL" to getting the sound right for the component he was reviewing. I knew "enough," but not like I do now. NOW, I know speakers must be ABSOLUTELY level - with each other. In my room, the tape measure says one speaker is 1/16" higher than the other. I ignore it. Why? Because the floor in that room (a new addition built SPECIFICALLY for audio in 2003) SLOPES between the right and left side of the room. MINIMALLY. But the speakers don’t lie when they reproduce the music now that they are exactly "in line" with each other. NOW, I know to tune by ear. And I know that moving a tube trap 1/32" can be the difference between really, really, really good... and superb. It’s not always the equipment that lets us down: sometimes it’s our lack of expertise/knowledge. When I look back at what I had then - and what I have now is WAY less expensive than then - I wonder what those components REALLY sounded like.
Now I have relatively good, but not super expensive stuff (I burned out on audio), but the sound, in terms of following musical lines, dynamics, airiness, coherence, are much more enjoyable on a system that is, combined, less than the cost of my VAC amps in the 90s.
An example of diminished - make that awful - returns on the investment: A local dealer has a $100k+ system, and I can tell you, he’s getting NOTHING out of that system that approaches the cost, never mind what that system SHOULD be able to do, musically speaking. In terms of sound, his system sounds (barely) like a $10,000 system (no insult intended: mine is around that much now), but a MEDIOCRE $10,000 system with no depth layering, no airiness, indistinct imaging and the dynamic range and contrast are truly pitiful. (Tonal quality is okay, but if the system was set up optimally, I’d be able to tell a Steinway from a Yamaha). So, yes, I’m disappointed in HIS system because I know what it COULD sound like, but it’s not the money that’s the letdown: it’s the dealer’s lack of either knowledge or just plain caring. He has lots of rich clients and they ooh and ahh and he sells a ton of expensive stuff. But he’s doing his clients a disservice. Sure, if you put Nordost Odin in nearly ANY system, it can be mind-blowing. But is it as good as the Odin gets? Not even close. Still, it qualifies as a "super expensive system." Keep in mind: he’s a dealer. People think of him as an "expert" in sound reproduction. He’s not even close to that. I doubt he hears much (or ANY) live music or he’d KNOW his system isn’t working. When The Rite of Spring has no more dynamic punch than a 60s rock album, something’s wrong. Yet people think "he’s the expert." If only that were true.
So: super expensive stuff set up poorly? The system will be Dead On Arrival. BUT. Half as expensive (but still VERY expensive) components set up RIGHT? Magic.