It gets easier with experience
A few more things gleened from 14 years of trailering our 23.5.We use some light utillity line to support the spreaders from the lifelines while trailering, so they don't bounce around on the deck. While raising the mast, we use these same lines to tie the shrouds to the lifelines to keep the turnbuckles from binding. If you use a simple basket hicth, it will slip as the shrouds tension and pull away from the lifelines.Always pay attention to the wind. Even with the sails in the bags, there is a lot of windage aloft that can push the boat to one side of the trailer as you winch it on.Those guide posts are very handy to get on the trailer straight. They can also be marked to indicate the depth of the trailer as you back down the ramp. But be careful, we once got them caught under the rubrail after launching and pulling the trailer out from under the boat.If you do forget to raise the rudder before retrieving the boat, do not back up.The only time I've "motored" onto the trailer, is when the marina requires that you tie up at a courtesy dock next to the ramp while you get the car and trailer. Then I've backed the trailer into the water, then motored the boat over and onto the trailer, although the motor is in neutral once you have forward speed, and I go as slow as I can while still maintaning stearage way.Mistakes happen when I'm in a rush to get on the water or on the road, so the first thing I do when I pull into the set up area is take a deep breath and mentally review what needs to be done. By the third of fouth launching of the season, I generally have set up time cut to 30 or 45 minutes, depening on how much "stuff" the family wants to stow on board. When the kids were small, I would expect to add 15 minutes to the set up time for each kid that was helping. Fair Winds,RobS/V Kinship