We spend a lot of time discussing the merits of how reproduced music sounds through various bits of kit. There's even an entire lexicon of terms to describe what we hear: warmth of tubes, analytics of digital, transparency of electrostats.
Some of the best listeners I know have some of the worst hearing; a few even have hearing aids.
Judging sound quality is more an exercise of the mind than the ears. Our ears receive the signals but it is our brains—our memories—that sort out the vibrations and make sense of them.
When we refer to an "experienced" or "trained" listener, what we mean is a person that has a wealth of memorized examples from which to compare and contrast live vs. recorded.
The best listeners I know of don't have better ears, they just have a library more packed with examples than others.
