I have absolutely no doubt that there is an AI tool that can do this. Heck, Apple music, Spotify et al are probably already implementing it. All of the Data already exists withing MC. Like last played, how often a track is played etc etc. Maybe its not the skill set for the MC developers (No disrespect intended) and what we need is different paradigm.
Yes, however you'd be mainly looking at YOU. The patterns for developing models, based upon things like listening data tend to require a relatively decent sample size of people.
Now, JRiver could collect this information, the problem is everyone's metadata is different, so the models would end up being ALOT dumber because a text string like "The Beatles" as an artist, only goes so far. They'd basically need to do what I do internally and resolve these things to more concrete "entities" For example, a 'track' is not just a track, it's a recording + composition (or compositions technically), with multiple participants (parties, or artists in more common parlance).
I'm pretty sure you could do some kind of CSV export from JRiver. I track all the playback activity my JRiver instances get (only for video) but it's external to JRiver (basically it's part of my wider, internal analytics setup)