Can you not accept that he may not be looking for high-fidelity or the accurate reproduction of the recorded signal? (which is why he chooses equipment that doesn't perform well in the test bench but sounds good to him)
No. He doesn't know what he is hearing. He knows what he is perceiving based on biases (including commercial ones), using his imagination, preconceptions of price, designer reputation, etc. I have tested myself and countless other people this way. The conclusions are almost always wrong.
You have to first do proper listening where you are only judging sound. Only then you can make inferences regarding whether the sound is better or worse, preferred, or not.
I have listened to countless types of tube and high distortion audio products that people say color the sound to one's liking. In vast majority of times the colorations and distortions are beyond just about any audiophile to detect let alone characterize as being coloration. In other times, they make things sound terrible as it harsher, brighter, etc. which no self-respecting audiophile would admit is "good."
Steve used to be an audio salesman so let me tell you a story about that. At our company, Madrona Digital we get reps visiting us representing audio companies all the time. A new rep came over one day and I asked him about his background. He said he knew nothing about audio when he worked at a high-end audio company but quickly rose to be the #1 salesman. I asked him how he did that. He said he would have someone come to buy a cheap CD player (this is years ago). He would show him one but before the deal was done, he would take him to a high-end CD player. All he had to do was push the button to open the drawer. The smooth operation of that mechanical motion was enough to make the customer pay thousands of dollars more for that CD player!
Similar story from years before that: I was talking to engineering VP at a large high-end audio company about supporting new high-def video formats (they also built AV products). He asked if he could get our help to build their own drives. I asked why? He said the sound that the drawer made was everything to them! That they spent huge amount of time researching the gearing and motor used to give that wonderful feeling of quality of that drawer opening.
Here is the kicker: that company's product was what that rep was selling!!!
We eat with our eyes, chefs say. Same for audio. Don't put value on faulty listening tests. Don't be a victim of marketing. Don't believe in people who don't know what they are doing.