The older I get the less impressed I am with any notion that reproduced sound is ever going to match 'the source'. I suppose, however, that that is the goal; but it is not my goal. Frankly, I don't think it will ever be a realizable, or practical goal.
Through numerous gear I've never, ever heard any reproduction (i.e. of a recorded musical event) that made me think, "Yes, that really sounds like Ella." Instead, my experience was always, "Yeah, it's the Memorex."
For me, the 'problem' with reproduction turns on the variance in the production--that is what I notice, more often that not. Whether I am listening to records or digit files, it is the production that annoys me, and often makes me unhappy. It is hardly ever the quality of the reproduced sound (I mean the difference in loudspeakers), which, in any case, my ears get used to pretty quickly. In fine, I tend to overlook/ignore the gear, understanding its intrinsic limitations, but instead concentrate more on what the producer was doing, at the console. Some do it 'better' than others. Some producers make a more pleasing product. I guess that is a personal preference, too.
That said, there is a point where the reproduction is low enough, or weird enough, to mask vagaries within the production. We want to avoid that. Probably a table radio or boom box is at the limit. Maybe a Bose 901. But reproduction on any 'decent' hi-fi is usually good enough to show off production values.
Also, there is a point in reproduction where 'what the microphone hears' is so far removed from anything that sounds realistic... that is to say, the performance that the microphone is attempting to pick up. There is a point where the reproduced listening experience becomes completely removed from reality. Here, I'm talking about headphones. The idea that a headphone can be 'natural' sounding in any way is an idea that has pretty much always escaped me. It is not the FR/distortion (and so on) that I'm talking about, but rather the experience of having sound 'direct injected' into the ear canals. Others certainly think differently. Headphones are now the big thing in hi-fi. I am not the customer for high priced headphones, for sure.
As an aside, when I was younger, headphones were never that important, for anyone. I would guess they really took off with the introduction of 'personal' sound--Walkmans, Discmans, and the later Apple digit-pods, now turned into cell-phones. We have a generation or two that probably only 'knows' sound via headphones.
Back in the day one could buy headphone-oriented 'binaural' recordings which were supposed to give a good facsimile of what the ears were supposed to have heard, within a natural sound field. I never listened to any of those, but only read about them.
Sometimes I think I need to get another hobby, but I might be too old to start anything new!