get PlayerPro... that dev implemented the ability to read/write ratings to actual mp3 files. both WMP and MediaMonkey id3 rating system. then, to make sure the ratings are same on both your phone and your computer, install microsoft's SyncToy and set up a two-way folder sync.
I guess so. I have WMP setup to auto sort music into a folder structure that maps to Artist > Album > [Track Number] [Song Title], and then I only synchronize the songs I've rated 4 stars or higher. That way when it syncs to my car (using my phone as a storage drive), I can browse the file system by Artist, Album, etc., and I only have the songs I like synced up.
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