iSm, it seems to me that you don't want to pay for the iPhone but are attracted to its, well, attractiveness. Personally, from your comments, it seems to me that you could probably get what you want in a much cheaper phone/plan, with or without a contract.
If you don't want a contract but want a capable not quite smartphone, Olivia (dd) has
the X-tc by Kyocera for $99 through Virgin Mobile. It is 3G and you can download Opera so you have access to real, not just mobile web pages. I think her bill is about $60 for unlimited phone/text/data (
review).
Virgin's (Helio's) Ocean 2 ($149) is supposed to be an excellent phone as well-- according to a friend who owns one and loves it
(review)
.
Sprint's Boost Mobile has the Motorola i9 which, although not a smartphone (like the Razr, which was my previous, previous phone and was really quite smart enough, to be perfectly honest), has internet capability (not sure if it's 3G) and lots of other features for $50 unlimited phone/text/data.
Sure, they aren't as sexy as the iPhone, but they do a lot of the same basic functions, including (important to me) push email from any provider.
If you're willing to enter into a contract or pay a little more for your phone (as I did with my Nokia smartphone), your options expand greatly and your pricing will be lower.