It is legal in some states to tow two trailers. It's not in South Carolina, Georgia, or Florida - mostly mid-west farming states. And you don't back it up.
We passed by alot of Troopers on the way out and back, so it must be legal in Nebraska. In Minnesota for non commercial the first trailer must be a 5th wheel, and I think the 2nd trailer has to be a boat. I know in Montana I've seen semi's pulling three trailers, that's gotta get interesting in inclimate weather.
I wish I would've tried to back it up in a parking lot. It can be done, you just have to think about 40 steps ahead. I've seen it done with two hay wagons, and those are by far the hardest thing to back up.