Windows only: Freeware app iTunes Sync syncs and transfer your iTunes music to non-iPod MP3 players.

As long as your MP3 player shows up as a drive letter in Windows (and most of them do), iTunes Sync will work. You select an iTunes playlists to transfer over to the device and go.

If you’re looking for more iTunes hackery, check out Adam’s guide to syncing iTunes to any folder. iTunes Sync is a free download for Windows only and requires the free .NET 2.0 runtime.

iTunes Sync [Binary Fortress Software]