I have Cat Trax. They work great. Now, how hard it is to push your boat uphill depends on the surface. If it is a hard fairly smooth surface, you can push your boat up a hill to the extent that you can push around 400 lbs up hill. It is easy to load your boat off the Cat Trax. I roll the boat up to the trailer. The Cat Trax are tied to my shroud wires; this is the balance point of the boat. This lets you get your bows 3 feet or so forward of the rear roller. Then I hook my wench line to the Dolphine Striker, tighten the wench to take all of the slack out of the line...a bit tight. Loosen my cat wheels, leave them in place then wench the boat on the trailer. If you are worried about the rear of your hulls dragging, you can lift from the rear center of the tramp frame, and push your boat on the trailer; this maneuver will depend on how much your trailer wants to roll without a vehicle attached.

I am sure any of the cat wheels would be much superior than the process you described. Cat Wheels are expensive. There are several ways you can construct your own wheels. Our club, took one of those plastic 55 gal barrels, punched a hole in the top and the bottom with a hole saw, put a piece of 2" pipe through it with plywood supports screwed to the barrel to strenghten the ends. They cradles were made from a piece of pvc pipe cut in half. It works!

David