Recovering music/syncing ipod problem

I hope you can stick with me as I try to explain this problem the best that I can!
My son has a 30G video ipod that is currently synced to a Dell with Windows 2000. All of his music/videos/games/photos/movies are on the ipod. Of course the PC crashed and strangely wiped out the music files, but kept the XML files that the music is attached to (?). So we have been unable to listen to the music on the computer because we get a message that says something along the lines of the original files are missing. (The movies are intact, and only one of the downloaded games have shown up.) He has only able to listen to the music in iTunes if the iPod was plugged into the computer. We kind of resolved the problem by doing this: with the ipod plugged into the PC, we made a folder on the desktop. Since we were able to listen to the music we highlighted all of the songs and dragged them into the new folder. Opening the folder we saw they were not xml files, but the m4 or mP3 files-something along those lines. We then unplugged the ipod and moved the files from the folder on the desk top to the itunes library, and we can now listen to the music without the iPod having to be plugged into it. However, there are about 750 songs on the iPod, but only 530 that have shown up in the iTunes library. What could have happened to the other songs?
To complicate things even more, my oldest son has passed his iBook down to him. I am going to reset the iBook to its factory settings so he can start with a clean slate. He obviously wants to be able to take his music from the pc to the iBook and sync his ipod to the mac. With all of this being said, could someone please help me do this? I feel like I need to resolve the first issue of the 200+ missing songs before dealing with the transferring of the music to the iBook (by the way, the purchased music is intact). Any help would be greatly appreciated!
Kelly

I went through my music and double checked what I was missing. Turns out its only a CD, and some songs that shouldn't be to hard to re-aquire. Also, I am missing an episode of Royal Pains [I have the second episode but the first one doesn't show up...]
I have decided to try and just replace the songs. So I found a different answer. ^^

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    * Need help recovering music on iPod/iTunes *
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