ITunes library won't download to ipod 20g

I have a library with music I purchased from iTunes and it won't sync to my ipod. it says it's syncing, but when i scroll thru ipod the music isn't there, it's still in my itunes library online...? i've read other posts, but none address my current situation. ipod is not on "hold"...??
help!
Frank

Update: I am running iTunes version 5.01.04 I was prompted to update my iTunes and this is the version it gave me. Everything worked fine before this update. Is there something about this new version that I should know in order to have my ipod automatically update when I plug it into iTunes online??

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