After upgrading my "analog rig" I also have to redo the LP's to my play list in order to get full benefit; that's what I'm doing now. I've got quite a few Pat Metheney records that look brand new, and I don't know what they sound like; that's a bad sign. It means playing that record is a waste of time, because I'm not going to add it to the play list; especially since I haven't heard or played it in years.
Today, I've heard a number of records that will be added to the play list that I don't own yet; all of those records happen to be "jazz jazz". I also subscribe to "Stereophile" because they practically give me the magazine. I think I bought 1 CD in 20 years, and don't even play that one. That lets you know how successful I've been in finding music there.
The best way for me to select music is to let the music select me. "I don't fight the feeling", and experimentation is out of the question, this means I'm walking a well worn path to success; no more wasted money. ( I've got way too many records taking up good shelf space, that need the boot) "What possessed me to buy that record"? is what I'm asking myself over and over.
The best path to success is "what ever works, and this is what's working"
Enjoy the music.