Terry...I'm busy as hell right now and can add a lot more but I'll shoot ya what I can.
Yes...run a faster ratio in the front. I did for years with great success. 10% faster is the target for a slower machine.
I like where you're going with this.
Light weight is pricey but good. I won a lot of races with light weight and less power than a lot of other guys.
I'm not a huge fan of D44's in the rear but it will work for you if you keep the weight down. A Scout 44 in the front is a bit of overkill for you but will last forever.
If you can...get rid of the front brakes from that 44. IH calipers are really fawkin heavy. Rob some parts off a Chevy 4X and put the (front) brakes on the rear diff only. You will have plenty of stopping power. I ran this setup for years on a blown alky buggy.
Front weight will hurt you with that short wheelbase. It will "porpoise" on you. Nose will dig then bounce up and so on. If rules allow...add rack and pinion steering and kick the front diff ahead 18" or so. Move motor and tranny etc. back as far as you can.
My mud Jeep....took so much weight off the front that it would go through the mud with the nose up about a foot. Almost zero traction up front...just enough for steering.
Nice motor but a little shy on torque. Run at least a 3500 stall converter. Run a tranny brake if you can....very important if you are running leaf springs. As you may know....the leafs will wrap up on a foot brake start and bugger up your IC and anti squat values.
For you...in a 200 ft pit...figure out all your gear ratios, engine R's etc to give you about 75 MPH wheel speed. Should be 1st to 2nd shift only in low range with 4.10 in the rear.
I build rpm activated air shifters for the autos. One of the best things I ever did for consistant times.
The D-20...almost as light as a chain drive....it'll work fine. I know guys running over 1000 hp through them.
Tires...My favourite combo...35X16X15 in the rear and 33's in front....gear ratios to match that will give you the 10% or so faster in front. This helps you launch straighter and helps pull straight through out the run. They prolly won't let you run cuts in the lower class.
Use alu wheels...as light as you can buy....try to keep the rotational mass down as low as possible. Cutting the tires will take over 40 pounds off each 35" Bogger.
Heavy tires and wheels are what kill most people. I will beat all their collective asses with light tires and wheels and plenty of wheel speed. You add the big weight and you need to add to everything else....pretty soon you have a 7000 pound monster that can't get out of it's own way.
Keep it light brother...if you decide to put something on your Jeep....put it on the bench first...if it doesn't slowly float up into the air....it's too damm heavy to add to your Jeep

I'll help ya some more if you need it....later...I'm swamped right now.