Hi guys,
Long time lurker just never much to add. This was my set up for many years. About a 30' travel trailer with a 14' tracker Jon boat on the truck with an older 8 hp mercury in the bed. Boat was only about a 100 to 125 lbs so not to bad to get on top, but to make it even easier I put a boat seat swivel on the back truck rack and attached a 2x4 to the swivel. Then all I had to do was put the back of the boat on the rack and secure it with a rope with the front of the boat resting on the ground. Then grab front of boat and rotate by walking to the front of the truck and placing on the front rack and securing. Check out eide boat loader at boatloader.com as a commercially made solution.