These worked slick at the boat dealership, plus it a tongue for pinning to a mower or 4-wheeler.
Those work great for whipping the wheelhouse around in the shed but on a tandem trailer not so much.
Hate to say it, but if you can move it in by hand, you should be able to get it with the truck. Just takes practice and you have to be able to back in with mirror.
Have someone spot for you until you get your recipe figured out.
This is the safest way. In a short time you will be able to back around the block, parallel park, and launch a boat while others are getting their’s ready at the landing.