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Hypotheticals here

I would go with the the carrier by you who has a better network, but that's more because I despite AT&T and their terrible, overburdened coverage here in the Chicagoland area. Despite being one of the largest cities in the nation, AT&T's coverage here is absolutely terrible. And what good is a smartphone if you cannot reliably access the Internet?
 
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Compare coverage maps in the areas you frequent and put the carriers in order of coverage. Then compare the plan prices. Once you find the carrier(s) with best coverage, pick the one with the best prices.

Then look up that carrier's phones and do a little googling to see if they have anything a lot better coming out in the next few months. If they don't have any big updates coming out for a while, buy their best handset. If they have something new and improved coming within the next few months and you can wait, then wait for the new phone.

Right now Verizon has the Incredible, AT&T has the 3GS, Sprint has the Evo coming in another 2 months at most, and T-Mo has the Nexus One. There are also new Dell Android and Win Mobile phones in the works as well as a new iPhone that will probably be on at least AT&T and possibly other carriers.

Choose based on coverage, then price, then pick your handset. Not the other way around.
 
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You do not pay roaming fees but if you are roaming more than half the time they may very well end your contract since you will be costing them too much money. Free roaming is a bonus for when you go out of coverage for an hour or two. It's not meant so that you can get some Sprint handset on Verizon for a cheaper rate. Your data speeds will be garbage on roaming as well. I love having it when I need it but I would rather pay more and get Verizon if the Sprint coverage was so bad that I had to roam all the time.
 
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