/me smooths down Blacksheep's fur.
I second the advice about going into a store and trying the models out. If you plan to do anything but make phonecalls, I'd stay away from windows phones. In general, I'd kinda steer you away from phones with windows on them, though windows 6 and up may be more intuitive (I have 5 and I think it is a poor interface for a phone).
If you like the iphone, you may even be able to get the first model for cheaper and it will work with the verizon network (it'll need unlocking though). The new iphone will technically work with other networks, but the 3g is not compatible with a non-at&t network, so you pay for something you won't be using. Yeah, you get a lot of bells and whistles, but if they don't get in your way and what you do use works very well for you, then it could make sense. I know when I buy technology, frequently I find myself using a feature that I never thought I would. For example, you are going to meet some of the myballard crowd somewhere. You don't have folks' actual names, let alone their phone number and you don't see them where they said they'd show up. You might find it useful to be able to use your phone to look on the forum to double check the location/time. Something you'd never do before, but since you already have the ability and are comfortable with your easy-to-use phone, it might open one more thing up.