I use a 1/2 ton pick up and a 14' box truck. The pick up has a 2" receiver hitch and the box truck has a 2" ball welded on the truck. It has the lights set up for standard 4 row plug. No brake set up, I have surge brakes on both my trailers. The 1/2 ton pick up has been new or almost new everytime I rented it.
I have a 22' Penn Yan inboard and a Helms 25 sailboat. Both are stored in my barn from Mid Nov to the beginning of April. Its a 300 mile round trip.
The best I can figure is that the helms 25 weighs about 3200 lbs. With trailer and rig etc I figure maybe 4,000 all together.
It looks like a 1/2 ton truck with the right package can tow up wards of 8,000 lbs so it looks like you are will within the limits.
Just the insurance question if the contract disallows it.