I have built systems where I chased details and ended up in very weird places. I usually didn't realize how weird until I quit listening to it for a while and then fired it back up a few days later. "Discerning" can have a lot of meaning in terms of audio reproduction. You can have stuff that's discerning in all sorts of different ways. By masking one thing you may be able to better hear something else. This seems like a win until you become very aware of the masking effect and suddenly find it unacceptable. Certain tonal colorations can make things pop, and this can get tricky because I've found some of these setups to sound tonally weird for the first few minutes but then I adjust and can listen in bliss for hours. Conversely I've found some setups to sound very open, spacious, and airy in the first few minutes but then become fatigued within 20 minutes. Too many early reflections in the higher frequencies I think. It sounds great at first but then my brain stops trying to interpret it and everything starts to sound flat and homogenized. It's complicated. As for specific equipment, it's mostly DIY speakers and various combinations of cheap amps in my case. Playing with a quickly adjustable EQ and then having your ears quickly making adjustments to your new settings can lead you down a rabbit's hole. I've been going through this lately - coming up with a killer EQ curve in the evening and then removing it after hearing it with fresh ears after a 24 hour break. I've listened to high end gear and heard ghastly sound in some rooms. At the last trade show I was at some of the best overall sound I heard (almost the best) was from $600 self powered bookshelf sized speakers with bluetooth built in. The best was actually from some $12000 bookshelf speakers which were being fed a signal from a cheap dongle dac off a macbook. That proved to me that a good amp and speakers can make a cheap dac sound fabulous rather than "reveal" the faults of the dac. Another close contender were some KEF bookshelf speakers. In all these cases I think the secret ingredient was small speakers listened to at fairly close range, limiting the effects of hotel room acoustical issues. If all your equipment is decent and nothing is hooked up wrong it should sound very enjoyable on almost anything you play through it. If it doesn't sound good, and especially if it sounds bad in a consistent way on most material, then I'll bet that's probably a room acoustics issue.
Is a highly discerning system enjoyable?
I argue that in terms of musical enjoyment, connection, feeling the musicians and composers maybe a highly discerning system is going too far? Maybe I want the warts airbrushed out. Maybe I like a system that lets me listen to a broader range of recordings without whincing?
Then there’s systems which are discerning of performances vs. discerning of upstream gear. I personally feel they are not the same thing at all.
Lastly, if your room is an acoustic mess, how can you tell?
If you feel strongly either way I'd appreciate examples of the gear that made you go one way or another.