Firstly, $380 across two years is less than the hardware costs. That is, it's peefarts compared to the psychic cost of saddling yourself with the wrong device.
Secondly...
Winner? T-Mobile G1.
Loser? Person forced to become a T-Mobile customer. True, at least, in this region, if not yours.
Thirdly, and most meaningless of all, is it just me, or is this whole idea of mapping out the two-year cost of a phone plan something iPhone-centric? This is the first time I've seen it applied to a different phone. It's like special math that only iPhone deniers like.
In any case, I'm hoping Android can do what the iPhone can't, which is present me with compelling reasons to ditch a Blackberry. (A shitload of Google Maps applications isn't going to do it.)