As for lifting a 19 ft boat, build a cradle for the stern. Lower the trailer tongue to the ground to raise the stern high as you can. Slide the cradle under the stern as far as you can. Raise the tongue on the trailer jack, and the boat will lift right off the trailer, suspended between the bow roller and the cradle.
You can make the cradle from a sheet of plywood cut to the form of the stern and built into a stand. Lots of ways to do it.
Before I had a cradle, I used an engine hoist / crane at the stern with a towing strap looped forward around the keel (C22 swing keel). Raise the hoist and lift the hull off the trailer from the stern with the bow resting on the roller.
You could use a floor jack with some blocks of wood too. In that case, raise the tongue as high as you can to lower the stern to the floor jack. Brace the stern with blocks of wood, raise the jack to lift the boat off the trailer, suspending it between bow roller and floor jack.
You could use the hoist on a boat up to 22 ft with shoal draft. You could use a cradle on a larger boat, but again with shoal draft.
Also, if you are gonna trailer sail this boat, you don't need bottom paint.
You can make the cradle from a sheet of plywood cut to the form of the stern and built into a stand. Lots of ways to do it.
Before I had a cradle, I used an engine hoist / crane at the stern with a towing strap looped forward around the keel (C22 swing keel). Raise the hoist and lift the hull off the trailer from the stern with the bow resting on the roller.
You could use a floor jack with some blocks of wood too. In that case, raise the tongue as high as you can to lower the stern to the floor jack. Brace the stern with blocks of wood, raise the jack to lift the boat off the trailer, suspending it between bow roller and floor jack.
You could use the hoist on a boat up to 22 ft with shoal draft. You could use a cradle on a larger boat, but again with shoal draft.
Also, if you are gonna trailer sail this boat, you don't need bottom paint.