Sync is not working right - folders not seen

My dad is using the latest version of iTunes with 10.6 on his laptop, synchroizing with a Nano. He's got some folders and subfolders for his audiobooks in iTunes. He has the options set to sync all playlists; when he synchronizes, it claims it copied everything (size-wise). But when you actually go to the iPod's menu by playlist, it only shows the first entry of each folder. What is going on - why isn't the iPod's playlist list mirroring exactly what we see on iTunes?
Mike

iPod Nano 5th Gen. User Manual
iTunes & iPod Hints & Tips

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