You bring up a good question. For me the answer lies in what kind of system have you built and are you listening to the system or the performance. For much of my history I was driven by my ability to analyze and hear more detail and nuance… in the sounds, images, soundstage, etc. The result was that it emphasized details and the venue and lost the gestalt and musicality which drew me in to the performance.
So, as I pointed out in other posts, with season ticket to the symphony for a decade I compared my system to the real thing and changed my system over time to be natural and musical. The music draws me in now instead of sticking out in my face. Different performances stand out, not by how they were recorded, but how they were performed. Much of today equipment is designed around detail and slam, making a sonic spectacular to wow the listener but failing to reproduce the musical experience.
To me a truly high end (audiophile) system reproduces the musical experience and sucks you in to the performance. It doesn’t make background instruments into solo performances and tell you all about the venue and mastering unless there was something very wrong with them. There are a number of companies working to produce equipment to do this like Sonus Faber, Conrad Johnson, Audio Research and VAC.