I guess I should try to word it different.
I am assuming you have a pintle trailer that you pull with the d-max? (if you are pulling it with the deuce it must be?)
The Max makes a ton more power so it will pull the trailer up to speed & maintain it where as a deuce is gonna take a while to get there and be bogged down quite easily.
The chevy is going to stay planted alot better than the deuce on the road do to the weight to contact patch area of the tires. ie- ground pressure (unless you add alot of weight to the deuce)
The brakes on the deuce do work decent whem properly maintained but do keep in mind they are 50+ year old tech. The ones on the chevy while smaller will probably resist fade better simply due to design.
I am not bashing your idea, I just think you might be dissapointed in the outcome of the truck after the work is done.
Fwiw, the trans is only rated for 300ft lb of torque so dont get to caried away on more power and heavy loads