The 'MacGregor Stomp'
Ah, that last two inches. This has been covered well in the archives, but I'll post again... I don't remember how the name was attributed (Trailor Sailor's BBS?), but I've always had great success with this method of scooting the boat forward on the trailer. Once you have the boat as far forward as you're comfortable with winching it, drain the ballast and go about unloading and preparing for your trip home as you normally would (lower mast, put outboard in tow vehicle, unload gear, etc). Attach the safety straps at the bow and stern of the boat- snug, but not too tight (The idea is to keep the boat straight on the trailer, but allow a little 'wiggle room'). On your way to the parking lot exit, get the vehicle up to about 5-10 MPH, and stomp on the brakes. The boat will slide forward, right into the stops on the front of the trailer's cradle. Take up tension on the securing straps for the ride home. Easy, no muss or fuss, and the trailer brakes do most of the work. If you think about it, you're applying no more force on any of your equipment than you would in an emergency braking maneuver. I used this method when we trailer-sailed our H23 for almost three years, and we loaded/unloaded about 30 times a season. We never took damage to boat, vehicle, or trailer when we used this method, but all were well equipped for the task of towing the boat. As for bottom paint, the only time I ever scratched or scraped up the bottom paint, I was loading the boat on the trailer solo, and the boat was not properly lined up on the trailer. A bolt on the bow roller caught the nose of the boat, and made a nice 6" gouge in the paint (and underlying gel coat). Never had a problem with bottom paint on parts of the trailer that were SUPPOSED to be touching the boat!

--Jon BastienH25 'Adagio'