Itunes will not load all songs onto my IPOD or start Itunes when connected

I have a new 80GB Ipod. Two problems I have noticed.
1. Itunes has 1609 songs. My IPOD only shows 1603. I have made sure all the boxes on the left colume of Itunes are all checked. Am I doing something wrong.
2. Just this past week when I connect my IPOD to my computer (PC -windows XP) it does not start Itunes. I do have that option checked. It connects fine when I open Itunes on the computer after the IPOD is connected or if I already have Itunes open then connect the IPOD.

Just try this on that one song first....the first one it stopped on.
Take it out of the itunes library list. If it asks about putting it in the recycle bin, say NO.
Then add it back into the itunes library. Will it sync now?

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