The auto's do much better with 4:10's towing. Your problem is not going to be going up hills if you get out of Florida, it is coming down. the OEM setup does not lock the torque converter going down hills and it just free wheels, requiring you to use the service brakes to slow it down. I have a 2001.5 4x4 auto that I spent a bunch of bucks on to beef up the tranny, keep in locked up and an exhaust brake.
If the tranny has not been beefed up and it has 165K on the clock, do not add power at this point.
1. Gauges
2. Custom Tranny
3. Torque Converter lockup box.
4. Exhaust Brake
5. 4:10 gears if you are going to see America.
If you are going to stay in Florida where the bridge in Jacksonville is the highest point in the state, then you will be ok for a while. Note however the the 47RE tranny was the weak link with the Cummins up front.
Over the years I have done all the tricks to mine: Gauges, injectors, tranny, exhaust brake, different turbo, chip, after market lift pump, steering brace, 3rd gen track bar(4x4), 4 low kit(4x4), more caster(4x4) and big exhaust(for cooling, does no increase HP) and Amsoil in the tranny and diffs!
I get in the high 11's or low 12's overall towing a 12.4K 5th wheel. 15+ around town and 19-20MPG on the road empty.
Chris