Difficulty getting full library to ipod

I have just bought a new laptop and copied my itunes library to this, I have now tried to update it and only 5gb of the 26 in my library has updated, any clues??
Advent 7088   Windows XP  

Mine did that too. It seemed to be one track that was causing the problem - iPod would update fine till it hit this particular song, freeze and then eventually stop altogether. I unchecked that song, also reset the iPod and it's fine now.

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    ?

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    TouchCopy Mac & Windows (iPhone and iPod Touch compatible)

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