The OP’s questions are good, although ’the real thing’ is slippery. In this case it seems to apply mainly to acoustic music in good sounding concert halls, classical music perhaps.
So what about rock for example? I go to rock concerts to get the live experience, the extra something beyond the recording and production in the studio. But for sound? Seldom. I rather listen to the best recordings and productions of the songs, in a good audio system, at home.
In this case, "the real thing" is to reproduce the music as good as possible as it was recorded and produced. Usually in the studio. With increasing emphasis on production, from the mid 60s onwards. Not just a good recording, but production as part of the art.
This means that you usually cannot hear "the real thing" in live setting. It exists only on the reproduction, the album or track. For example, I cannot hear I am the walrus, or Strawberry fields forever, in a concert, even if all the Beatles were alive and well today. What I can do, however, is to get such songs to sound as good and "real" as possible, compared to the intention - from the producers, engineers, and the artists involved.
I use large bipole speakers (Audiokinesis Dream Makers) that excel in reproducing live concerts and a three dimensional sound, with very good timbre and tonality. Live recordings are often a joy. Still, for the best sound, I usually go to the studio albums.
On a basic level I understand what the OP is talking about. I play a c flute, alto flute, and some guitar, often trying to play along with the music reproduced from my system. There is certainly a distance, between what I hear from the live instrument, and what I hear from the playback. Especially with the flute. Even if the distance is smaller, with the best recordings.