IPhone Settings Not Sticking in iTunes

My iPhone settings are not "sticking" in iTunes. Also, all of my contacts have duplicates in iPhone and Entourage. However, they are fine in Address Book. I wanted to simply write over the database on the iPhone, but I can't get that to work.
Is this a corrupt preference file of some kind? How do I fix it?

I would recommend removing iTunes and Quicktime (and the Apple driver) and reinstalling it.
As for overwriting the iPhone, you can reset the sync history and check "PC overwrites iPhone" in the advanced section of the Info Tab in iTunes.

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