I row a 14ft metal boat with uhmw bottom, there are a few pics here in some posts. The second boat is 1648 metal jet.
I have dragged both through boulders/gravel/steps/etc and onto a trailer.
If you mean pulling on from a dry parking lot or "unimproved launch," I do it often.
I suggest two things for dry loading a weighty hull/motor: 1st an electric winch on the top arm of the trailer, there is a cable version, don't know if there is a strap. Make sure it has a welded gusset!
2nd, a tilt trailer. If you want to get it good and slick, get some uhmw strips on the bunks. Keel roller is good, make sure the bow eye is capable of the pressure. Often it takes some jarring with the cable pulled tight.
Take out the fishing gear and load in your truck before if you are on an incline. A broken cable , when sprung tight, can take out an eye or cut off a digit! This is not an exaggeration.