Well, of course the iPhone works with iTunes, they're both made by Apple and they made a specific effort to integrate the two products well with each other.
I highly doubt one exists for the BB. It would require a plug-in to install on your PC with your media player, and going over wi-fi... I would guess the demand is simply too small for a developer to muster the effort to start on something difficult like this.
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BB Wishlist:
-Gmail BIS integration with an effective 2-way read/unread sync solution
-Better integrated alarm (on legacy devices)
-Threaded SMS
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