HT1386 I sync all songs, photos and videos between my computer and iPod classic with no problems, but when I get to sync info I get this message: "iTunes cannot sync Calendar and contacts to iPod. Try logging out of Windows adn then logging back in".

I sync all songs, photos and videos between my computer and iPod classic with no problems, but when I get to sync info I get this message: "iTunes cannot sync Calendar and contacts to iPod. Try logging out of Windows adn then logging back in".  Could you please help?

Correct. When you update via iTunes all synced media that is not in your iTunes library will be lost.
As IO said before:
You can redownload most iTunes pruchases by:
Downloading past purchases from the App Store, iBookstore, and iTunes Store
I do not think it included audio books.

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