Problems with iTunes 7 (Mac OS X)

Upon installing the newest version of iTunes 7.0(70), several songs in my Library failed to sync with my iPod mini. When iTunes attempts to copy the songs to my iPod I get an error saying:
(Name of song) was not copied to the iPod because it could not be found.
I found the error very annoying, because the songs that the message referred to, played fine within iTunes, and when I looked into the iTunes music folder (in Finder), I quickly found the songs within the appropriate sections.
I know that the format of the songs is not the problem because prior to this version of iTunes the songs never had a problem being synced and played on the iPod. Now when you try to play the songs on the iPod, the song name appears on the screen, but nothing happens when you click it. Any suggestions?
iBook G3   Mac OS X (10.3.9)  

And I forgot to add that this problem only happens to certain playlists, but does not affect the library.

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