Why does new 60g ipod download some songs but not others?

I have a lovely new ipod and have inherited my son's itunes library on my XP user account. I removed all the stuff of his that I didn't want and was all set to download 600-odd tracks on to my new ipod. Unfortunately it only transfers about a third of the tracks on each album and unaccountably skips some altogether. Also, it will only transfer 50 or so songs and then "freezes" on a particular track. I then have to close down using Windows Task Manager, re-start the computer and delete the track in question before the repeating the whole miserable process. There must be a better way mustn't there?

Thanks for the suggestions, but I ran updater and installed the latest itunes yesterday to no avail. Also I think it's unlikely to be an unsupported file type problem as some tracks and not others are transferred from the same album.

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