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I can't believe no one has mentioned this as a possible solution. If anyone has played around with the software they might know that by going in to OPTIONS->PREFERENCES->IPOD SUPPORT->TRANSFER SETTINGS->ADVANCED and then unchecking USE IPOD MANGLED FILENAMES will allow you to write transfered songs to a different folder than the ipod would generally use. Yes, if you uncheck this box the songs with get written to your ipod, they will show up in your ipod's playlists, BUT they probably won't play.
Sure it would be awesome if this setting did work because we all know that apple uses some screwed up method for sorting your songs on the ipod's hard drive.
So, to fix your problem just check that little box and the plugin will use ipod's "mangled" file system instead. Next you should delete all of those files from your playlists and then finally look in the ipod folder in windows explorer and delete any music files or music folders that are not in those F0 thru F49 (or whatever).
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