Double towing is no problem and my Motorhome is 47' long. Got pulled over in Ft Myers for doubling by a state trooper. He wrote the ticket out wrong with the wrong fine and told me it was a moving violation. Drove 15 miles down the road and hooked back up. We left after new years and drove back and passed 20 state troopers in every possible situation and never got a second look. Called Florida to pay the fine and it was only a $100.00 & it was not a moving violation (does not effect insurance ). I also drove all through KY and TN on that same trip....no issues. As for pulling the boat, it's not for everyone. You have to plan ahead. Be prepared to use your horn and lights to clear a path when turning.
