When you are no longer young, as many of us are, We all have a database in our listening history of our favorite music. Many of my favorites have been heard thousands of time over many systems, using many sources.
You know when it is good, and that is what makes me smile. I just calculated that I bought my first serious system in 1969/70. That is over 50 years, or 2,600 weeks.
I know when to listen to the decay of cymbals, or sustain of guitar. I have become much more sensitive to source materials. And I look back and smile at the journey and how lucky I have been.