Be cool, get a Droid or Blackberry on the verizon network with unlimited data.
My bill for 2 blackberries, 1000 minutes, one of them with unlimited texting and the other with 250 texts, unlimited data, insurance, other small add ons is approx. $170-190 /Month depending on my international usage.
Buy iPhone 4G for $199, sell it on ebay for a lot of money. Use said money to buy Nokia N8 (when it comes out) for $494. Have a better phone and pay $15/mo for unlimited data.
Or get a Droid on Verizon and have a better phone and network for the same money.
Or buy an iphone from VZW and have the best network and most user friendly smartphone with the highest resolution screen on the market.
I payed 150-160 for 2 iphones, but recently dropped them to lose the data plan, went down to 90-100… I think i may go back to them… its worth the 50$ IMO