Pleae help ipod Nano wont update, error message driving me insane!!!!

I have a 2nd gen ipod nano which after originally connecting to itunes was fine, has now decided to not update and not even allow me to restore. I keep getting message that I need to type in administration password. The other message says unknown error .
If you can make sense of this please help.
thanks
Mac Mini   Mac OS X (10.3.9)  

I am having a similiar problem... I could not transfer all of my songs due to an "error -69". Anyone know what this might mean?
I'm very frustrated!!

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