I'm surprised no one has mentioned this:
If you don't want to contracted in, you can go to Walmart and get a pay as you go smart phone. Unlimited talk, data, texting, everything, for 45-60 dollars per month, depending on which one you get. That's what my wife and I did. We were sick of paying $160/month for two smart phones with limited data. Now we pay $95/month for two smart phones with unlimited EVERYTHING.
Cons in doing this:
-There is a limited phone selection. I personally think they are fine for my purposes. Probably will be for you too. But you will get more selection in a contract with me f the major carriers.
-the phones won't come with a warranty besides the factory warranty, which is probably only like 30 days. So buy a good case for it.
Pros in doing this:
-You will never be contracted in (it is month to month, you just buy more service) which means no hidden fees, no extra fees, NONE of that bs, which AT&T did every single month to us. Verizon did the same before I got AT&T.
-Depending on what phone you get (mine does this, my wife's doesn't) it might work off of both AT&T and Verizon's towers, rather than one or the other. This ensures you a better chance of having good signal wherever you are.
-You save money every month. Instead of paying that extra in a phone bill, you can shoot more. No brainier, right?
-As I said, you get unlimited everything for a flat rate.
-You still get a smart phone. My wife's has 4G whereas mine only has 3G, which is fine by me as it is sufficiently fast. Anyway, since you're coming from a flip phone, it will be much faster anyway :P
I could prolly go on, but I think you see the point. No, I'm not trying to sell you anything right now. I just whole heartedly believe that, now that I know about Walmart doing this, there's absolutely no reason for me to ever go back to a stupid contracted big name carrier.
Always have clean socks.