Problems with downloading new songs

I loaded my iTunes with songs and downloaded all of the songs to my 30g iPod, it worked beautifully. SInce that time, I have loaded new songs to iTunes, it worked beautifully. However, the new songs won't load to my iPod... no error messages or anything. It just won't load.

Thanks for the help! I found a way to "fix" the situation but it's not a good one. My son's iPod was originaly loaded from this machine's iTunes. When I connect my iPod, it still thinks that it's my son's iPod. So when i try to download any new songs, it appears to be workig but doesn't load the new songs. However, when I reboot the computer with my iPod connected through the USB port, iTunes appropriately identifies my iPod and downloads the new songs as expected. How can it get my iTunes account to appropriately identify my iPod without rebooting? Is there a setting somewhere? Thanks!

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