I enjoy listening to music because it evokes emotions. In my experience using my system the sound between analog and digital is very close and I can listen to either for hours.
There are certain recordings I’ve compared analog to digital and when they are the same file it’s hard for me to distinguish the difference; however, I have noticed some recordings where I prefer the version and sometimes the version I have is LP and other times there’s a digital version that I prefer.
Finally I often wound if my preference is based on the emotion evoked or remembered as a result of listening to the music.