Very wise and interesting post indeed thanks for the reading...
You forgot one thing, and it is not a criticism from me just a rare fact and possibility you did forgot to mention ...
Some products of the past were some flagship among the best in the world...They created a sound experience of their own and were never redesigned again as it was...
My AKG K340 is exactly the case... When optimized it beat most headphone save the very costlier top ...It cost me 100 bucks... I wrote a review of 30 pages about it ... 😊
My amplifier a Sansui alpha from 35 years ago in a lesser degree is a product of high quality even with today standards and he cost me 300 bucks....
I tried last week to upgrade it with one of the best contemporary amplifier for headphone for my K340 a very well reviewed one ... It was a disaster for me ...I returned it...The Sansui alpha is not obsolete in this coupling at all even from the headphone out...This speak a lot about his design quality...I must say to give justice to the "upgrading" amplier brand that the K340 is probably one of the most hard headphones to drive well...Too picky and not only hungry...If they are not fede well you loose his potential S.Q. AKG was a microphones designer they created this hybrid as they created their TOP microphones line , and anyway headphone are reverse microphone or the opposite... No other company after that ever bother to create a son complex and costly design for headphone...This is what a Top russian headphone designer said to me...
Coupling the two, the Sansui alpha and the K340 give me audiophile top experience for peanuts... Anyway i never listened anything better by a good margin... On almost all acoustic counts..
Then....
Price tag is a deception most of the times as the UNIQUE indication of S.Q. quality because material design quality is one thing but sound quality is not linearly related to it the way most people imagine .......Material design quality matter for sure but it is not synonym of sound quality...
It is not an absolute essential unique indication for audiophile experience conditions which implied synergy between chosen gear FIRST and SECOND acoustic, mechanical and electrical precise well embeddings of the system parts into one another and also in the room/house/ specific ears relation and grid...
Use a low cost flagship of the past and embed it well and the result may be as in my case top audiophile experience... Because a MINIMAL quality treshold of sound experience quality exist objectively and subjectively...
There are LOTS of affordable products that perform right on the edge of the most expensive esoteric units. By affordable, I mean what most working adults are willing to pay if the sound is worth the price. That means a used Sony table radio for some. A used Yamaha receiver and a pair of Elac or Warfdales for others. It may mean a lot more. Careful used shopping can of course pay off.
If I were to define the minimum of what I consider true high end sound excluding prestige or hearing damage level playback, I might suggest:
Audiolab 6000 integrated, Sonas Faber Luminna IIs, SMSL Do300 DAC, Monoprice sub. Some kind of streamer, Wiim or what ever that thing is. Cables form Monoprice, Amazon etc. I venture that is 99.9% of what is possible. That last .1% is a real bugger. Real, but hard.
That is still several thousand dollars which is a lot of real money to most of us, but it is actually high fidelity. Is the IOTA or similar as smooth sounding as the Autiolab? Or spend a bit more for a Hegel? You hit the diminishing returns real fast. Mojo or Aries DAC worth it? How far short is a JDS Atom amp from the most exotic headphones amp? Not much. Is a $9000 preamp any better sounding than $109? I would not bet on it. Prettier. Nicer feel. More inputs. Maybe your choice of masking distortion. But not more neutral. I do sort of miss the masking of my Nakamichi preamp with it’s tone controls. Nostalgia maybe.
Unfortunately prestige, looks, and ego drive the high end market. Usually you do get great sound. Some of it real, much of it placebo. Both making you happy. Hopefully you get reliability. Want a lifetime amp? Buy a Mac or Bryston. Billet aluminum cases don’t sound any better. Braid over a power cord does not improve imaging. VU meters are eye candy only. No amount of user end electronics can make the source better. They can only degrade it. Some degradation is considered to be "musical". Some is not. Some is a tradeoff we are willing to make not to get a different defect. Personal preference.
Yea, I would put a set of $50,000 speakers on a RadioShack receiver and the next best dollar spent would probably be better speakers, it there actually are any.