Will one copy or iTunes work with 2 iPods?

A friend, who has the same kind of iPod I do, the 4th gen 20GB click-wheel, has asked me to help him with his. He's unable to get anything at all put on it by his copy of iTunes, which he recently downloaded and installed.
I'm thinking I'd like to try his iPod with my iTunes on my computer. (Both he and I have Win XP.) But can iTunes work with 2 iPods with no problems? Can I sync from my library to his iPod, make sure that it plays on his iPod, then restore his iPod? After that I suppose I'd have to reinstall the latest software version, 3.3.1?
So a bunch of questions..
Thanks

Zevoneer wrote:
There are a few different ways to use two iPods with one computer, have a look at this help page for suggestions: How to use multiple iPods with one computer
Thanks! A big help.

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