Hey James!
I didn't read through the other responses so I may be repeating, but I always tend to be the "go-to" guy when my friends and family need phone advice :innocent:
Let me tell you up front, in order to be happy with your phone choice, you HAVE to 1) Know what you want out of your phone 2) know what the capabilities of said phone are and 3) what are you willing to pay for your "price to satisfaction" ratio. Explained further:
1) What are you going to do?
a. Do you even need a smart phone?
b. Is it for any sort of formal use (ie not just texting friends)
c. Are you set on getting a smart phone because you want to be a person with a smart phone? (no way is this an insult, it's completely fine)
2) Capabilities
a. iPhones only differ by generation. Getting one allows you to purchase blindly and know you're getting a great phone "overall" without having to really pick and choose
b. Droids are SUPER powerful phones
and very user friendly. But if you don't pick the right one you'll hate it
c. Battery life is much better on any iPhone. Droids aren't as good but you can purchase a spare battery and wall charger cheap. I always have batteries laying around and never think twice about it (I spent $30 for wall charger plus 2 extra batteries)
3) Cost
a. You pay a premium for any Apple product and most of the good Droids. Are you spending more to have the "latest and coolest" or you spending more to have a better product? Either can satisfy this but buying an older generation iPhone/Droid can certainly save you some money without sacrificing much
b. Buy a cheap Droid and you'll have a crappy phone that'll lag, be lacking in updates/support, not be any fun to use
I know I kind of rambled but the only way to be happy with you phone is to know what you're getting beforehand. The only way to do this is to ask yourself questions, then find out if the phone can do that.
My suggestion: Droid Incredible 2. Excellent software, cheap (~$100), and sexy appearance
EDIT: I just thought I'd share something else. My mom never used anything but her old razor for years and is knows nothing of technology. One day walked in for a battery and walked out with a Droid X all by herself. Figured out how to do everything on it including sending me an email bragging about it. Tell THAT to someone who says iPhones are the only easy phone to use