Over here Verizon is the best to get coveragewise. Cingular sucked (I couldn't even get voicemail because my "mailbox was corrupted"?!) plus the coverage was bad. Verizon is the only provider with which I can place a call from my neighborhood, since there are no nearby cell towers until 2004. They're a bit more expensive here, but IMO you get what you pay for...
Many kids I know haven't had any good luck with Sprint either. Maybe it's just something in Massachusetts. Whichever provider gives you the best coverage for the best price, go for it. Don't worry about the phone though, or going with one provider just to get a certain phone. IMO the phone itself isn't as important as the provider.