I suspect there as many different answers to this question as there are different people with different tastes, experiences and expectations. When I started in this sandbox, call it 1970, the "high end" was still emerging--and I jumped on the tube bandwagon relatively early. I still have some of those same components to this day--used in my vintage system. And I can tell you they do sound good- a pair of old Quad 57's that were restored, along with a pair of Quad IIs with top notch glass, a restored Technics SP-10 that I've owned since new. In fact, I'd say partly due to the restoration of the Quad Loudspeaker and its synergy with the Quad II amps (I was using ARC tube amps back in the day), this system has never sounded better. (I'm using a modern arm and good cartridge). It is not analytical or "revealing" in the sense of clinical sounding- if anything, it makes things sort of homogenous and "comfy," like a well broken in leather baseball glove. It's great strength is its apparent transparency-- I say apparent because that system seems impervious to noise and gremlins that can crop up in my high efficiency horn system.
All that early high end stuff- the ARC, Levinson, big Infinity loudspeakers, Krells, etc. were pricey in their day, but today's uber high end has taken pricing to another level. Worth it? Maybe, if the combination of components is "right" and set up properly in a good sounding room.
We know a lot more than we did in the early '70s (at least I do) and things like turntable set up are far more advanced, to extract that last iota from the groove.
There's always been a degree of audio nervosa in this hobby, but at a certain point- whether its budge, time and energy spent searching for the next "great" thing or simply burn out from the endless churn of "gotta have the latest," I relaxed about the gear. My main system is very satisfying. I know what its short comings are, and accept them. I appreciate that there is always another mountain to climb, but one of the things that got me out of the endless "quest" was my interest in more obscure records- early heavy rock, post bop jazz-- stuff that wasn't necessarily reissued, let alone by the usual "audiophile" houses. Yeah, I appreciate that Tone Poet did Katanga! and that Craft reissued Woody Shaw's Blackstone Legacy-- those are not easy to find as OGs. But a lot of the records I listen to are not audiophile showpieces-- they were made at a time when vinyl was still a mainstream medium but the quality of plastic and pressings were all over the place.
To me, it is a mindset. I think part of it is also your point of entry. I have shelves of audiophile "spectaculars" that reside, largely unplayed, on my shelves. I'll pull something out occasionally -- like an old Decca classical record-- and really enjoy it. But, for the most part, I've managed to shift my focus to the source material, rather than the playback gear. I have little interest in impressing anybody with sonics-- I'd rather play them the "Same Old Rock and Roll" from Roy Harper's Stormcock (Jimmy Page on 12 string).
As to the @soix car analogy, I've owned many Italian exotics and a well set up Miata can give you amazing thrills if you are willing to cast aside preconceptions. I don't think you need to give up your audiophile "card" by appreciating what you have, assuming your system does what you want--for me, it is utter transparency in the midrange, fully fleshed out bass (that was hard, and required work on a number of fronts), as well as getting inter-component noise down to a minimum (running 104db speakers).
I've heard a lot of big, fancy systems over the years and a lot of them left me wanting--I think so much is that elusive "synergy" which is very hard for me to comprehend in the abstract. I do know it when I hear it, and it has less to do with price than with the "right" combination of components, set up effectively in a given room.
Sorry I did not have time to make this shorter.
Bill Hart