A833 OD or 727 behind a 440. Suggestions and questions

The combo is going in a 64 D100. Truck has peg leg 3.91 but, I have 3.23, 2.94 and 2.76. I'm adding a sure grip to one of them. If manual, I would have to get all the clutch stuff and the 727 floor shifter. I think the cost is going to be about the same. The 727 is freshly rebuilt from a car/truck and not a motor home. I do like stomping on the accelerator and my other D200 383/727, gets a lot of it. I'm trying to make the truck road worthy for taking road trips, cruising and such, not driven daily.