Wow, Tom. I knew of the 250GB cap, but I didn't know that included upstream. That's going to be tough for your roommate, Tony, since in order to keep that nice ratio of his, he'll be using more upstream than down.
On the whole, though, I agree with many that 250GB is actually pretty reasonable. However, I think it's only reasonable right now. In the future, I see a lot more content becoming IP based, and I think the ISPs are really preparing to price gouge us when that happens. Between VOIP, AppleTV, Netflix's expanding library, XBox's online marketplace, and services like OnLive, I can definitely see that limit being reached, and reached legally.
Thank goodness you don't have Time Warner Cable, Tony.
Do you not have FIOS in your area? I can testify that it rocks.
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Matt