Three things I’ve learned about listening.

@bikefi10 I do the exact same thing, but with wine.  

1) Ill play not so great recordings of music I like, and Ill usually acclimate to the sound quality or lack of. Usually a couple beers will help that. 2) Ill start off with not so great recordings of music I like then progress to my better quality recordings. Its like an instant upgrade.

Some of this may just be the equipment coming up to ideal operating temperature which does make things sound better.  My system takes ~half an hour to get good.

Try this...,

From a "cold" system, listen to a disk and after it is over, go back and listen to the first song again.  To me, it always sounds better than the first time (better imaging, less glare).

4) first:  stop talking. 🙊

"3. If it sounds really good, leave it alone!"

And what if one track sounds really good, and the next one, not so much?  There is so much variability in what the media presents.

Other than using eq, I’ve set my speakers up for a range of music by including 27 different "profiles" in the crossovers available at the flip of a couple switches.  You quickly learn what profiles work best with what tracks.

OP, ..."3. If it sounds really good, leave it alone!"

That is a good one. I realize, typically I get to the point where I am really happy. After having gone through an upgrade cycle. I've done the cables, speaker adjustment, etc. Then I leave it alone... for six months or a year. So I know the sound inside and out. Then I work on speaker placement  again...or vibration control, or some aspect I have not really worked at. And I get a notable improvement. My skills for fine tuning have increased after really spending time with my system. Then I leave it for another year and then attack some other aspect. Over time... it just gets better and better. This assumes, you have gotten all your components perfect and synergistic and are happy with them.