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.