Gray ! on 100 records when I sync with new version of iTunes 10.2.1.1

I have a Ipod classic 30g. I have 4079 songs in my iTunes. I am using Windows 7 on an ACER Extensa. I have my music on an external hard drive. The same place it has always been. Since I upgraded to the new version of iTunes when I sync my Ipod it randomly marks 100 records with the gray circle with a ! in it. Showing that it is not connected. I check the songs are still on the drive in the same location. I go into the control panel of my computer use the repair function and all the ! are gone. As soon as I try to sync iTunes selects 100 songs and does not sync them to my Ipod. After the first time I added more songs and there was no change to the number of songs not synced. Any suggestions?

I only have songs no other media. The specs for my Ipod say it should hold 7500 songs. This problem only started after upgrading to the newest version of iTunes 10.2.1.1

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