I recently acquired an XBOX 360, and the first (and only) thing that annoyed me was that I could not use the playlists or ratings from iTunes without somehow transferring them to Windows Media Player on my PC. It was cumbersome, at best. I suppose I can’t expect a Microsoft product to natively work with iTunes, so I was prepared to write an application to sync playlists, ratings, and whatever else from iTunes to WMP.
After searching Google several times and finding nothing, I finally stumbled across Music Bridge. It does exactly what I need, including:
Perfect! I can now set up a cron job to perform this sync every night, or whatever.
The link above is to download.com, but there is more information here.