I'm the crazy towing fool, and I wouldn't do that one. As a tandem-tow, I MIGHT do it... But like I said: I'm the crazy towing fool.
The biggest problem isn't the weight of the Willys, it is the weight of that trailer empty. Those open car haulers are good for AT LEAST a full 2000 by themselves. I would be surprised if the willys weighed in at more than 2500, they were pretty small and sparse on the running gear, so even all-steel they should be light... Unlike anything Chrysler has made in the last 15 years.
But at 2k for the trailer, maybe 2500... 2500 each to be safe with the willys, you are at 7500.
Now you are also asking your little 4-in-a-row to tug itself, at 4500 lbs... and you hit the big 12,000 lbs GCW from everything. On a 4-cylinder? I wouldn't. Our CRDs are the same exact truck as what is the "euro spec" with the 7000 TRAILER rating, so that puts us at 11,500 for a GCW. And I've done exactly that with that big 6840 lb generator I pulled, and the CRD was happy as a clam at 19mpg. Pushing to the Euro spec is a normal thing, b/c you are mentally adjusting from the idiot-lawyer-written book that matches our CRD with the wussy V6 gasser. Ours is MUCH more powerful b/c we have TORQUE.
To the guy who suggested renting a truck to do this job... I wouldn't do that either, unless the trailer is a 5th wheel. This needs to be done separately. Tongue weight would NOT be a problem, the engine of the second Willy is over the axle, so all the weight of the first one is split between the axle and the ball... Which to me is too MUCH tongue weight. It is dang hard to do, but the best way to load a trailer is BALANCED, or slightly nose heavy to avoid ANY excessive suspension changes (heavy or light) on the rear axle of the tractor. Since it is so hard to do it properly, the conventional idiot-proof idea is to load all trailers nose heavy by a lot, which can and does also cause sway by lightening the front wheels too much. Hence the added "logic" of the great unwashed of "Gets ya a truck with a longer wheelbase" which does nothing to solve the underlying problem - the trailer is not loaded properly.
Want to talk about sway and what causes it? Ask me about bringing my EMPTY 7.5x20 enclosed trailer (small car hauler size) from south Florida to Savannah. 2600 lbs, and it swayed all over the road b/c it was designed to have TOO MUCH tongue weight BEFORE anything was loaded into it. Why? B/c with it's designed use, 4k lbs of car would be stuffed into it and centered over the axles, shifting the center of gravity to the rear, and stabilizing the trailer. But with nothing in it, it almost put me into the ditch several times by "wagging the dog" and b/c my front wheels felt so light.
Tongue too heavy... Tongue too light... Either way: WRONG LOADING. Try again, thanks for playing!
