I'm sure anyone who has to deal with cell carriers would say it was a pain in the ass. But that pain also kills off a lot of competitors. Much of Loopt's success is traceable to the fact that they were one of the few groups, if not the only one, who were both great hackers and willing to endure endless meetings with cell carriers.
It's sure one hell of a sustainable competitive advantage if you have the cojones to pull it off. That being said, I'd rather spend my time thinking about how I'm going to get my users laid rather than how to appeal to the self interest of a non-rational corporate entity.
update: That is, I work for a big company and you come to me and tell me that you're going to make my company a hundred million dollars. I say, gee, that's great, if this works out then I'll get my name on the wall and maybe a small bonus. And if it doesn't then I'll get fired, I won't be able to pay the mortgage and my wife will divorce me. So whatever your question, the answer is no. To make it work without a huge reputation and network and existing relationships you need to rely on a lot of luck.
My general outlook on this is that if you read Horatio Alger, the general formula is luck, pluck, and virtue. Which is great, but what's even better is if you can minimize luck and make your bread-and-butter off just pluck and virtue. Then whatever luck comes your way is just icing on the cake.
