I don't think he'd even be considering getting a smartphone if he couldn't afford the data plan in the first place, guys.
My family all has Droid 2s and we each end up being worth around $60 for unlimited everything. Im not sure Id get another Droid though. These are pretty glitchy but for all they can do they're bound to have some flaws. I heard Razors are pretty badass, iPhones are supposedly pretty cool too.