IPod dosen't synch to iTunes

A friend has just gone from using a PC to a laptop. All of his music is on an external hard drive. He's downloaded iTunes to the laptop and imported all the music from the hard drive. When he connects his iPod all the songs get the grey exclamation mark next to them and a message comes up saying none of the file paths are valid. His iPod is then erased.
When this happened the first time, we uninstalled iTunes and deleted any related folders and re-installed it from scratch. We connected the iPod to the empty iTunes and went through thte process of making sure the iPod and iTunes would recognise each other. Then we imported the songs from the hard drive again and made sure in Advance Options that the default file path for the music was changed. We also resotred the factory settings on the iPod. When we connected the iPod again, all the file paths in iTunes were losts and the Advanced Options was showing the default c: drive music path. We ejected the iPod and closed iTunes and when we opened it againall the music was reconnected and the files paths correct. Connect the iPod and the same problem.
I don't understand it at all.

Did you try to consolidate the iTunes library? http://docs.info.apple.com/article.html?path=iTunesWin/9.0/en/15329.html

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