I guess I'll be the loaner in the MD camp. There is no comparison in the hauling capabilities of a pickup vs a medium duty truck. I assumed from your name you were a big time farmer hauling bales and other stuff around. I have customers that are farmers, and the ones we've convinced to go to MD trucks and semi's haven't looked back. Those trucks are just built better for the abuse the guys put them through. The ones still using pickups always seem to be running the things ragged and the shit is always wore out. I'm not sure what the insurance difference is, but I imagine it can't be too outrageous or I'd hear about it. But if you're not loading it full and hauling heavy, and you need the cab space of a crewcab, those f350's are still a plenty capable truck.