Is it possible to really know what you're doing?

I remember when cd players were all the rage. I read an article about the Micromega stage two. I managed to get one and behold best sound player I’ve ever heard. It was so musical. Unfortunately it was not reliable. Thus began my frustration. It took 25 different players before I found The sound. Ended up with a Meridian 508.24. Not sure it was as musical as my Micromega, but it was as close asI could get. So my point here is, this hobby can be frustrating if you are looking for that  particular sound. 
 

For me it seems no matter what equipment you have at some point I think you get bored. So to counter that, I have 6 amps and 12 pairs of speakers. So when I get bored I switch out something. As been said, at some point you just have to enjoy the music. The journey ends when You end it.

I think very very many here are very happy with the music systems they have put together...

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).

Trial and error is part of the fun IMO.  Listen to lots of different components and you will know when something sounds good to you.  That's all that matters.

@cleeds Easy on the common sense, bud.