Error 'songs were not copied b/c they cannot be played on this iPoD'

Help!
My PC crashed and I restored a backup of my music to my laptop. I installed the newest iTunes but when I went to sync my iPOD nano (first generation? I think) I got the above error. Over 2/3 of the songs wouldn't sync. The error listing says the file type is not supported by the iPOD. All of the files are MP3 I ripped before. They are all playable on the PC. I have restored the ipod and reinstalled iTunes and re-started everything. All the software, firmware and Windows XP is fully up to date. The info on the songs list MPEG format convered with iTunes 6.xx. I have re-imported several and this did not help. I have used the 'convert to MP3' function that is available on some of them and this did nothing. What's up?!! Is it true that the earliest Nano's are not functioning with the latest sofware? Help!

What is the format of the songs that won't copy. Some of the earlier iPods would not play Lossless or other types of files.
See these Articles:
http://docs.info.apple.com/article.html?artnum=93867
http://docs.info.apple.com/article.html?artnum=61476
Determine the 'Kind' of the songs within iTunes and post back with more information.

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    See these Articles:
    http://docs.info.apple.com/article.html?artnum=93867
    http://docs.info.apple.com/article.html?artnum=61476
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    See these Articles:
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    http://docs.info.apple.com/article.html?artnum=61476
    Determine the 'Kind' of the songs within iTunes and post back with more information.

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