The wifey and I have a 2 year Verizon contract. Its due to expire in May of next year. I've got a chance to rake in a good BoGo deal on a very nice phone.

Does Verizon allow you to upgrade a phone or do you have to wait for the contract to run through its period?

you can upgrade at anytime. you just may not get the discount.

As a former salesman in the wireless game, The best way to do that, is to go in and bitch to a manager. Threaten to cancel your contract, say your going to at&t and going to get the data package with the iphone(assuming you don't have the data package currently).They wireless providers make maddddddd money off data. It sucks you have to be a dick to get what you want accomplished, but Cell providers make it that way.