LOL You are a brave soul. Be careful and make sure you check State laws as I believe there are quite a few state that make towing like that illegal. 5th Wheel to Conventional is legal or so I heard. Nice Truck by the way! Getting ready to sell my F-150 for a larger truck.
I don't think I'm more "brave soul" rating than anyone else that tows medium to large size travel trailers on the highways. When set up properly, the double trailer rig handles the same as when towing just the travel trailer. Just have to allow more clearance for turns and lane changes.
I also keep a real-time visual of my boat and boat trailer with a wireless backup camera that I've attached to the rear bumper of my travel trailer.
You are 100% correct about state laws. Every state has its own set of laws with respect to non-commercial double trailers. My rig is illegal in 22 states!
My plan is to stay in states where I am legal when double trailering.
Here is a general overview of where you can double trailer.
Some of the "green" states require that the first trailer be a fifth wheel configuration. I think Michigan, Wisconsin, and a couple other states have that special requirement.
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