You can "train" yourself how to listen, and gain enough experience with systems and components until you become adept at recognizing what sounds "wrong" versus "right", versus what you like. Some people ramp up faster than others, just like everything. Then you pile on basic literacy in electronics and acoustics - more specifically for hifi audio - plus some diagnostics ability, and the right mix of skepticism plus open-mindedness (good luck) - and voila, you sort of know what you're doing!
Just like in my career, asking questions has been completely useless and ineffective 99% of the time for me, lol. A.I. won't help with that. Focusing on what I'm doing, plus sum of experiences over time time, is what does it for me. My listening "skills" were also a damn mess for a long time because I was drinking too much (quit 4 years ago now).