were they songs that you purchased with itunes? if so, he needs to be authorised to use them before they are transfered on to his ipod.
how did he import the songs from teh jumpdrive to itunes? did he put a copy of the music on his hard dive then add it to the library, or just stick it in and import off of it? because there needs to be a complete copy on his computer, just importing it will not work.
in response to troy, yes there was. all compatability issues should have gone away with one of the last two upgrades.
if you absolutly must, winamp has ipod support built into it now.