HT1351 When syncing music playlist from my itunes to ipod, I get a message saying some songs couldn't be found. Why is this - they are in my playlist.

When syncing music playlist from my itunes to ipod, I get a message advising some songs could not be found. Why is this, when the songs are in my playlist.

By design, the organizer (and any other database management systems) is there to prevent you from duplicating your media files. The catalog management allows you to have the same image in different categories or albums. Duplication in different folders is to be absolutely avoided.
The same image file can have multiple tags like 'family', 'vacations', 'birthdays' and be present in three different albums with the same names. On obvious advantage is less disk space. Another one with your present folder system is that if you edit one of your duplicates, the other ones are unchanged.
I don't see an easy way to make your present folder structure simplified for the organizer ...

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