Skipping Songs in a 4GB Nano

Merry Christmas,
I've spent the morning trying to figure out why my son's new iPod won't play all the songs he just loaded. Of 75, about 25 played. I went through the five Rs, then did the following:
1. Created a new playlist in iTunes for the songs he wanted on the iPod.
2. Synced the iPod to this playlist only.
3. Dragged songs to the playlist one at a time, starting with songs purchased through iTunes.
4. Checked the iPod after every five songs to ensure play.
He's now able to listen to the songs from iTunes, but once I add songs imported from a CD, the iPod starts skipping the songs purchased from iTunes. Very odd. Could this be a permission issue? A file type issue?
Any ideas are greatly appreciated.
iMac FP 17"   Mac OS X (10.3.9)  
iMac FP 17"   Mac OS X (10.3.9)  

Resolved by updating iPod software.

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