Dubdub,
Great Post !! I cant count how many of my friends and inquiring minds, that always asks, Who do you have for your cellular service? And of course I tell them, just because I choose Verizon, Oh I can get it cheaper with another provider. Well, I tell them go right ahead.
The most important thing like you mentioned is, is it going to work sufficient in the geographic area you live, work, travel, and play in. And then of course, does the provider have the services you are looking for i.e.: Type of cell phone, data link, camera, and all the other bells-and-whistles that are offered with the type of device you are looking for.
Im far from a rich guy, but I have no problem paying a little more for something that works better for me! I have a box full of cell phone and a few PDA, I have tried and moved onto something in my eyes, I thought was better for what I needed. And I guess most of all, you have to feel comfortable with what you are use to operating.
Good Luck With The Choice You Make,
Matt