5hp Off-road redneck firewood hauler thoughts with background, would it really work FOR ME?

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And lots of gear reduction which can get expensive quickly
Expensive, and lossy. I get what Jags is saying, about pulling a semi with a weedwhacker, but at some point, the losses involved in the (assumed) multiple gear reductions will cause the system to reach a point of diminishing returns. Gear loss is proportional to rotational speed, and while the drive wheels are turning slowly, that input shaft connected to the weedwhacker drive unit is not!

A real mech.E (not me) could probably estimate the reduction ratio at which more input does not equal more output, for this tonnage and input RPM.
 
Sounds like a lot of fun, if the budget and time are there for it. But 20,000 lb. loose payload on 15% grade... just don't kill yourself!
That would be my concern. OP says all downhill and part of it is 15% grade. From what I see, pulling the load isn’t as much of an issue as handling it with a vehicle of substantial mass so the cart doesn’t roll over the horse.
 
This has all the signs of a tragic death that could/should have been avoided. I haul a full cord, or a bit more, on my 1991 f250. It has been upfitted to do the job safely and reliably. There is no way I would think of taking a load through what you are describing. Power is not your biggest problem, traction, stability, and ground pressure are. 20,000 lbs of wood? Do you know what it takes to safely carry that on a smooth road? It takes 10x more to do it on a rough trail. A 5 ton truck (m35a2)is a beast and would have a rough time hauling half of what you want, and that is a 6 wheel drive diesel with low gearing.

Moving 20,000 lbs of firewood down a steep grade with a home built "jalopy" is a darwin award waiting to happen, and it won't have to wait long.

If the road has gotten that bad that fast, then it needs fixing and people need to learn how to drive so they don't chew up the road/trail.

I can build anything, but even with materials you have to find parts. I'd have to have a hell of a boneyard to scrounge and a steel mill to build what you are describing. Just the cost of welding (gas, wire, rods, electricity, etc...) is going to be expensive. This isn't something you can cheaply build your way out of.

Based on what you describe...
20,000 lbs is going to require tracks, a winch, lots of power, an engine brake, and a lot of skill, because the vehicle is going to weigh at least 10,000 lbs by itself, probably double/triple that.

Fix the road, learn to drive without destroying it, and make smaller trips with something that is more ground friendly. That's my view based on what you have said here.