1) The bow dragged along the metal beam the front roller is on and left a trail of gelcoat dust.
2) When the bow got past the metal it broke the wooden centerboard support cross bar. It was only a 2x2 with a notch cut in it so not very substantial in the first place.
3) When I was winching it back on (still hitched to the car) the autobailer drug a trench in the grass and in the process knocked itself loose. It's still attached and appears undamaged, but it's loose and can twist.
Would preventing the tilt trailer from tilting, or unhitching make things go smoother?
When I have to do this again to put the centerboard back I'm thinking of cutting a board to fit from the front roller to the aft roller to give the bow something to ride on. I'll replace the centerboard support after the boat is back on the trailer. I'm not sure what to do about the autobailer. Maybe put down a couple of 2x4s for the hull to ride on instead of the autobailer.
This image shows in progress of winching it back on. I've added a couple additional boards to try to prevent dragging the bow up the metal beam. The centerboard support broke when I off-loaded.