Moving iPod to new PC.  Songs not found.  iTunes doesn't recognize iPod

Actually, it is a new Windows install on the same machine it used to be on. We have a recent back up the iTunes folder but the total size of that is about 900mb. There is about 9mb of content on the iPod though. iTunes doesn't find music and opening the itml.xml file from MD\MM\iTunes shows paths for "unfindable" music being things like:
C:/Ipod/F05/Nickelback%20-%20How%20you%20remind.mp3
Stuff purchased on iTunes still plays after re-authorization since we just copied the iTunes folder back over in to the new machine.
Keeping the play lists is very important.
Questions:
1) How do we get the new "machine" to recognize the ipod as being associated with this one instead of the old install?
2) How do we pull the music that iTunes in Windows doesn't see anymore back off the iPod and in to the places on the hard drive where iTunes is looking for files?

No, first of all i've got a MacBook not with dual core
I suspect an error with the connection type 'cause at work i receive this kind of problem and at home not.
I solved the problem with the ipod updater yesterday, at home i successfully updated it but today i get a new error message while contacting itunes server:
I cannot process the request, an unknown error occurred on itunes server (error type -206)!
Do you know why?may it depend by the Office server?
thanks
MacBook 12"   Mac OS X (10.4.8)  

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    I suspect an error with the connection type 'cause at work i receive this kind of problem and at home not.
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