I found the listed curb weight at 2,273 pounds ('71 CJ5 Universal) so you are pretty close. I'd agree that your weak point will be the truck engine, transmission, and GCWR. However if you are within that tolerance the truck should be built to do it.
Your Redwood max GVWR (if loaded up) is 16,500. Jeep would be 2,273. Truck 9,200 or so (loaded up with passengers, fuel, etc.). Total on all that is 27,973. Sweet! Assume you have the Crew Cab 4x4 your GCWR is 30,500, so you should be good to go if you want to try it. I had a 2012 F350 DRW with the 6.7 engine and those things are beasts.
That would look pretty cool motoring down the road!