1st Gen Crew Cab Engine

This is going to be a truck first, right? For that you're going to need beaucoup torque and gearing to move whatever you hook up to. That's why I voted for the 383. Hooked to a granny gear 4 speed with 4.10 gears you could tow the Queen Mary in first gear. The 383 should be a little cheaper to buy/rebuild than a 440 and give you better mileage to boot.