I'm just glad I read the whole thread - I see people trying to tow up here like that all the damn time. Don't they cover rigging trailers and loads in driver's ed?
As much as I hate to say it, there should be an endorsement on driver's licenses out here to legally tow a trailer - showing that you've learned how to properly rig and balance the load.
As far as you goes - it's easier to use the Jeep than to move it by hand (I used to have a hand truck that was modified to mount a ball - you'd put it under the ball socket, tilt back, and it would pick the trailer up so you could move it. Don't use it on loaded trailers, tho...) and it was a real backsaver.
Yeah, if you'd taken that out on the road, I'd be surprised if you were able to steer at speed. Not much contact between the front tyres and the ground. Any idea what it weighed?