Will not transfer songs to iPod from iTunes Library

I'm using an iPod mini (without video) and trying to sync with music on my Windows 2000 desktop. I've ripped music from my CD's and added them into the iTunes library. I'm saving my library on a network space. I plug in my iPod and auto-sync. The iPod appears to be syncing, but does not actually add any music. All the songs have checkmarks next to them, so that's not the problem. I've also tried to manually manage the music and drag the music to the iPod and the same thing happens. It's synced up the playlists I've created, but there isn't any music actually transferred to the iPod.
Any suggestions?

I updated the software on my iPod Shuffle and now it does not recognize any of my songs from the iTunes Library that were previously easily available. All the songs, except two recently added cd's, have an exclamation mark next to them. When researching, it says the files are no longer found ... I have to physically inport each song all over again in order for iTunes to recognize them ... what a pain that will be ... not very happy. I should not have updated the software and avoided all the hassle with re-importing my music. also not sure how to remove all of the exclamation marked music in my iTunes library. Not sure if this is the same issue you experienced??

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