ITunes does not agree with iPod

I am trying to update my iPod (20GB version 3.1) i have about 14.5 GB of music. When I started trying to update the music last night i had just erased all the music off of the iPod so it was completely empty. I plugged it in and went to sleep when i work up it had transfered a little bit of music over night but my computer had reset itself overnight. I reopened iTunes and only about 35 songs had been transfered. When i plugged it in iTunes said that it has 7.32GB of music already on it. but then directly below that it says that i have 143MB of music on my iPod and my iPod says that as well. SO now when i try to put my music on there it says that there is not enough room and that it wants to put a slected playlist of music on. The iPod says it has 18.5GB free. I do not understand why they are not corralating. I am running on version 5 of iTunes. someone please help me!!!! I am leaving for a trip in about 24 hours and i would really really like to have a working iPod with me.

Welcome to Apple Discussions.
Restore the iPod, and try to sync again.

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