I'm of the opinion that Apple made the right choice in keeping their brand clean from all the privacy issues with those free ad-supported services, opting instead for classical b2c relationships (service to client in exchange for money) with the implied privacy protection of typically confidential business to customer relationships.
It seems like Apple could retain these benefits by including a MobileMe subscription with every iDevice, but not making it outright "free". Once 90% of iCustomers have MobileMe accounts, Apple would be motivated to improve it and add more Google-like cloud syncing.