iTunes Sync will let you synchronize any iTunes playlist with any MP3 player that shows up as a drive letter in Windows. iTunes Sync is designed and tested to work best with iTunes 8. You can configure as many different MP3 players as you need and synchronize each one with a different iTunes playlist. You can use standard playlists or dynamically updating smart playlists to synchronize your MP3 Player.
Windows Server 2008,
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