That whole rig weighs about 325Lbs, just bulky. I wasn't hauling a trailer into the French Quarter for the night.
I don't see anything wrong with the boat in the truck. A flag on the tail end and you are good to go. Maybe there are some states that require lights, but any I've checked don't have limits on how far you overhang the bed as long as there is a flag if extending 3' or 4' (varies in some states). There are stricter regs if you haul on larger highways or toll roads sometimes.