My strategy for syncing my music library with my phone is that I have four smart playlists: - songs rated 5 stars which I haven’t listened to for at least 8 months¹ - songs rated 4 stars which I haven’t listened to for at least 16 months - songs rated 3 stars which I haven’t listened to for at least 32 months - the 20GB of least-played music (there are some other strictures as well, like eliminating Christmas music a…
It's called "long time no see" and it includes any songs I've listened to more than 10 times but haven't listened to in the last year. I've been using the same music library for nearly two decades now, so it works really well for me. It's like a constantly rotating nostalgia playlist.