Will she be eligible for the iPhone when her contract expires on 12/17? If so, it might be worth it to just deal with the dumbphone for the next 3 weeks and get her the phone she would really like. As much as I would never own one, the iPhone is probably the best choice for a "non-power" user.
I'm looking at upgrading my original Moto Droid to either a Razr or the new Google Galaxy Nexus... but having trouble justifying the $250 - $300 cost.