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Why do only some of my songs in playlists sync to my iPod?

Why do the songs in some of my playlists I've created in Songbird (running on Windows XP) sync with my iPod (nano, 4th gen.)? Some playlists only partially sync and some never sync even though they are supposed to. I can see the name of the list, but there is nothing in the list. I've got them set up to automatically sync. I've got plenty of space on the iPod.
 
indifferent I’m perplexed.
Inappropriate?
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