Moderate risk?

[wyoboondocker]

Hey all! I've been in search of a used 5th wheel toy-hauler under 30ft and around 20k. Finding that they are scarce as the proverbial hens teeth but the shorter bumper pull types are plentiful. I' quite experienced at tandem pulling my boat behind my current 5th wheel and would like to continue to do so with the toy-hauler. Question is...Can tandem hauling behind a bumper pull be made reasonably safe? Boat is 17ft Tracker walk through and haul vehicle is Ram 3500 SRW. Looking to keep toy-hauler at 28ft or less and hardside. Anybody out there with experience in this endeavor?

[RAMer-Jammer]

In many US states, you cannot legally tow behind a pull-behind trailer, only a 5th wheel.