I double towed for a couple of years with either my 2 place jet ski trailer in back or an open trailer hauling my Polaris Ranger. Both worked fine. My 5th wheel was a 29' Laredo and I towed with a 2001 Chevy 2500HD with an 8.1 in it. The setup worked and towed well but you have to remember it is very long. Gas stations can become an extra challenge. Parking lots for stops along the way can be a challenge. When you arrive at your campsite the 1st thing you have to do is figure out what to do with the back trailer. I would bring along a hand dolly purchased from Harbor Freight in order to be able to move around the back trailer. A lot of campsites won't have room for 2 trailers and a tow vehicle. The hitch on the back of my 5th wheel was custom made by a friend and very heavy duty. Did it all work - Yes. Was it a pain at times - Yes. Was it worth it to take my toys to some very fun places - Yes.