ITunes wont sync after first sync from start up....

I'm having troubles with my iPod 80 gig
First off, I can sync the ipod if I add the new song, movies, etc. then restart the computer. Upon restart, it will open itunes, sync it, and then idle. After this, I cannot sync it again w/o doing the above processes.
Secondly, the ipod or itunes is not fully syncing my library. It won't sync mulitple songs from the same artist if there is only one album listed. It will only sync the one song that has the album listed. For example...
1) Alice Cooper - Steven (song) - Welcome to my nightmare (album) (successfully added to iPod)
Alice Cooper - I'm Eighteen (song) - No album listed - (Was not added to iPod)
But, if the artist has multiple albums listed in the library, it will add all the songs, even ones that have no album listed.
I hope this is clear, its hard to explain but annoying to deal with.
Windows XP
Windows XP
  Windows XP  

I recently reinstalled and I had a few errors when it installed. It asked me to put in the CD labeled 1. When I did, said it couldn't find it but kept installing anyway.
that might be our culprit.
i just went searching at Microsoft, but couldn't find anything relevant to that sort of message. (no guarantee that there isn't anything there ... i might just have been looking in the wrong places.)
so it might be worth heading to your PC manufacturer's website to see if they have any specific troubleshooting advice on installing XP Media Center on your particular make and model of PC.

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