Raising the mast
I have a 1979 O'Day 23 with shoal draft. I kept it in the water, but trailered it to locations I wanted to sail until a year ago when I moved up to a 30' Hunter. I raised and lowered the mast by attaching a small block at the bow, running a 3/8" braided line through the block and attaching it to the fore stay. I ran the line back to either winch, attached the mast to the step with the rear pin at the step. Then with help to keep the mast from running off to port or starboard, I winched the mast up to vertical and installed the forward pin at the mast step. I would keep tension forward on the mast until my helper could connect the fore stay to the forward point -- done!!. To lower the mast, I just did all the above in reverse while feeding the line out past the winch to lower the mast to the point where my helper could catch it. I also made two mast supports to hold the mast while trailering, rather than resting it on the pulpits. This method did take a bit of muscle to pick up the mast and move it forward after it was unpinned from the mast step, to place it in the trailering position, but the whole thing only weighed about 75#. The only investment was the small block which was attached to the forward bracket. Good luck.
