H John, can't see why not as long as the tow vehicle is man enough and the driver is competent. When I was in the army they ran courses teaching us how to tow safely. We used to have a road to the officers mess with two bad bends on it and it ended in a small roundabout. They put us in a 3 ton bedford (actually 5 and 1/2 tons designated 3 to permit us to drive it) with a two ton steered trailer on `and we had to reverse down the road, round the roundabout and back up. When we mastered this they would then put another trailer on and we learned how to do this. Agreed the army had the time, manpower and money to devote to this, but it was a great way to learn.
Don't know if I could do it now though, that was 1965!!!
By the way we used to do skid training on the barrack square when it was covered in packed snow. Great fun and a great way to learn safely.