Jayson,
For the price of a lower end HT, you can get a lower end 2M mobile like the Icom 2100H, Kenwood TM-271A, or Yaesu FT-2800M. All are priced in the $150-$200 range.
HT's are great if you backpack a lot, or live in a metropolitan area with lots of repeaters nearby. But when on the backroads, 5W won't get you very far (10 miles at best). This problem is made even worse if you use the rubber dickie antenna inside the vehicle. They also get quite hot after a moderate length QSO. The other issue with HT's is the audio quality, both on transmit and recieve. The small speaker inside an HT delivers substandard performance. The standard condenser mic isn't quite so bad, but I prefer a speaker mic so my head isn't right next to the HT when transmitting.
Setting up an HT to work well and comfortably can cost more than buying a mobile. A speaker mic adds about $30, and buying a 18" 1/4 wave/ dual band antenna adds another $30. Believe me, you will want to replace the cheap helically wound rubber duckie the HT comes with! Add another $30-$50 for the 12V power cord if you don't want your batteries to die after an hour.
A mobile comes with a decent mic, power cord, and a speaker somewhat better than the one in an HT. The only extra expense is an antenna and mount. I bought a simple 5/8 wave 2M antenna with 3/8x24 thread for $25. A cheap CB bumper mount and length of coax can be had for less than $20 at Radio Shack (you got questions, they got blank stares
)
Try looking around at a hamfest for a used mobile. You could find one on E-bay, but I've always been wary of used equipment and e-bay in general. Most of the catalog and internet merchants offer used/demo radios with a limited warranty, but you'll only save $20 or so.
If you're saving up cash for a rig, wait a few extra pay periods and get something you'll feel happy with, instead of settling for less of a rig.
Hope this helps. Feel free to ask about anything else, and WELCOME TO THE HOBBY!