Too bad you're in SC. We've got 4-5 trucks on our lot that all fit what you'd need, as long as you don't need 4X4. One or two would probably be a little above $5k but they're flexible.
Nemaha Valley Motors in Seneca offers Chrysler, Dodge and Jeep Vehicles
Check out the 01 dodge cummins dually, the 95 ford flatbed dually, the 95 ford crew cab dually, or the 94 chevy with the service bed. And if you want a REALLY nice 1/2 ton, the black 96 GMC used to be mine.
As mentioned above, the stop and go with a load would kill most 1/2 ton automatics, but there are some heavy 1/2s out there that could handle it. Stopping could be made adequate with the use of trailer brakes, but if you're doing it repeatedly they could overheat. Depends on your route I suppose.