I have found on my Mariner (19ft, 25ft mast) that raising the mast solo requires a system that prevents the mast moving off the intended track by the wind, and can hold the mast in any position while I futz with shrouds, forestay, etc. I studied various rigs people had come up with for Catalina 22 and the Mariner (both very common boats).
I ended up with a gin pole with a latching 2-way trailer winch mounted on the gin pole. My 1st gin pole made from a 2x4 wasn't strong enough and caused me to dump the mast part way up. My 2nd gin pole was a 2x6 with the outside of the mast crotch reinforced with angled metal along the corners. My next lesson learned the hard way was that I needed to prevent the mast swaying horizontally in the wind while going up/down. The Mariner has aft swept shrouds so the mast has no lateral support until almost all the way up. My solution was baby stays which I attach when raising solo.
The jib halyard attaches to the gin pole. The line to the winch goes through a block at the end of the gin pole to a block just behind the forestay eye to a cleat on deck. Going up, I winch the gin pole down to near the deck, which pulls the mast up to vertical. Baby stays eliminate the horizontal sway until the shrouds take over.
Mariner-specific, the aft (top) end of the mast, supported on a crutch on the rudder gudgeons, needs to be raised from the trailering position to a higher starting point so that the mast clears the cabin sliding hatch when the base is put in the tabernacle. Another lesson learned the hard way.
Much, much easier if there are 2 people. I simply walk the mast up, no winch or baby stays needed. 2nd person keeps tension on the jib halyard until I get the forestay pinned.
Trials on the trailer in the yard instead of at the launching ramp are highly recommended. I have never used a crane. But the gin pole, crutch extender, and baby stays go with me wherever I trailer.
Fred W
ODay Mariner 19 Sweet P