Listening (as opposed to hearing) is a skill that can be honed even if you’re hearing isn’t stellar. IMHO....any critical equipment evaluations should be long term if you’re trying to decipher subtle differences....high end, or even just "good" equipment. Otherwise, you’re essentially just getting acquainted with a system during an initial listen. Not a great time or method of knowing much about what you just heard, yet that’s the extent of the exposure many of us have to gear we don’t own. It’s not so different than when you first meet people.....some you can get a bit of a feel for initially, but it can take a while to get to know a person (or a new system) well enough to make any long term decisions about their finer points.
You can’t really understate the significance of a room, and the synergy that a system within the room has on the overall impact of the sound. That’s one of the reasons I don’t have much faith in A/B comparisons, or evaluations done in an environment where you’re not intimately familiar with every aspect of a system.