Conneting old iPod to a new iTunes library

My brother got his iPod stolen recently. I have an ancient one, probably one of the first generation iPods, that I never got rid of. I want to give it to him until he can afford a better one.
My concern is how this iPod will recognize his iTunes library. Will the iPod erase his library? Can this be done? Is there anything particular to watch out for? I was just going to hook it up and see what happens but I don't want to wipe all the songs in his iTunes.
There are some songs on the iPod but he doesn't care if those get erased. He just wants to be able to use it with his existing iTunes.
How can I do this?
Message was edited by: kjh22

I have a similar problem. My ipod is not quite so old, it's a 3rd gen. 8G nano, but I can't get it to sync "completely" with my new laptop. I have about 700 songs on the ipod, but only 41 have transferred over. Also, it's going from Windows XP (desktop), to Vista.
Could that be my issue?
If so, how do I get my desktop library onto my laptop?

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