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.

This reminds me of my smart playlist on Apple Music.

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.

Love that you've got archival stuff and Christmas music filtered out - feels like everyone with a big library has a few odd folders that shouldn’t be in regular rotation