The way I go about it is I look up others' terminologies and for specific recordings that they say exhibit X, then I correlate with my own experiences with similar.
One thing I've found helps is background listening, weird as that sounds. Some things just jump out at me when I'm not actively looking. Could just be alleviating fatigue from extended concentration.
The above aside, it helps to have a mix of good recordings (low detail, soundstage, natural timbre) and poopy ones. Helps me figure out what's in the recording and what's just the gear. Mindful listening always helps, as does not stressing.
For some reason I've found some background noise helps me better discern detail at times (depending on ability of gear to resolve). Could just be me being weird.
Pick songs that you know really well, listen harrrrrrrrd, repeat lol. Or pick one song and listen to different aspects over time with each repetition. Quick AB back and forth are more confusing than helpful to me.
@brencho That's what I do now but I get lost in all the details. I use YYZ but I think it's too complicated to listen for specific qualities, or I'm not good enough yet. I was doing quick a/b and like you say I think it does make it harder to tell. I think the main issue is not having enough experience.
+1 on quick A/B'ing being counterproductive. What helps for me is to make notes, and take your time. Come back to things a day, a week etc later if you have that luxury, then compare the new notes to the previous notes afterwards. So much of perceived differences can be attributed to mood, health etc at the time of listening.
A/B switching can be useful to avoid mental distraction of making the change with cables, etc. Don't set time limits or A/B rapidly unless there is a particular sound that stands out differing. @Imraan point about perceived differences should be heeded; I've experienced this frequently as well.
I use a player with A/B repeat feature (e.g. Neutron) and listen to short song snippets in a loop. As an example, to assess timbre and detail resolution with cymbals, I listen to a 20 second snippet from Diana Krall's Boy from Ipanema, starting from 1:50
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