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 and some music files I have in my library more for archival purposes than anything else, but this is a decent approximation).

This gives me a reasonably fresh selection of music and at least at the moment, with my daily sync habit, when I listen to a song it goes out of rotation for a while which could be anywhere from a week to years.

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1. This was originally 6/12/24 months, but I ended up boosting that time frame as storage grew tight on my phone.