Update freezes on old iTunes MP3s

I just got my second 8GB nano in two days. The first one would not update - - it kept freezing during its update on particular songs. I decided the first ipod was defective and exchanged it for an identical one. I also have an ipod mini and an ipod 5GB original. I've never had a problem loading music on either of those - - ever.
Same thing keeps happening with the second one. Here is a song example that hangs the update:
The Pump - Larry Carlton
Encoded with: iTunes v3.0
Bit Rate: 192kbps, Date encoded: 10/11/02
Anyone have any ideas. So far I've been deleting the files it hangs on but its a pain because I have to nuke my iMac during the update, reboot, then it has to write all the hundreds of songs to the ipod all over again to find the next one it hangs on, all at USB speeds (vs Firewire...)
Help???
G4 iMac Mac OS X (10.4.7) 8GB 2nd Gen Nano

Try recreating your iTunes library, and see if that helps...
How to recreate your iTunes Library
Also, try this on one of the songs that doesn't transfer (it hangs on). Right click it and go to convert selection to AAC (or MP3). Does the converted version transfer?
btabz

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Message was edited by: CoJeff

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Update freezes on old iTunes MP3s

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