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Hum. I use a mac, so perhaps the iTunes for the PC is somewhat different. One thing to try is when you go to on My iPad, click on sync. Another thing to do is go to the book tab on the on my iPad and see what books are listed. I normally sync all my books, but you can select individual books on this tab. Then select sync and see what happens.
One thing that I've noticed can cause issues is when you get low on memory on your iPad and you don't have enough memory to sync.
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