Here's how I do mine. I use a custom made 8' long 2x4 with roller at the top that fits into the transom gudgeons. The idea is to get the mast up at roughly 45º. It's easy to lift from a horizontal transport position up onto this tall crutch from the cockpit. Then it's pretty easy to roll the mast from resting on a custom pulpit mount up the roller until I get the mast base at the step, pinned with 1 step pin. I then make sure that my asym spinnaker halyard which goes to swiveling cam cleat on the mast, is clipped to the stemhead fitting. This is my safety net, in that I can pull on this and hold the mast up to then go futz with forestay. I also put masking tape over the upper and lower shroud turnbuckles so they are standing up in more or less final position. Do similar with the triangle plate on the backstay, so that this does not get itself kinked. Then I stand ON the cabin top, facing aft, straddling the mast. I can bend knees and cradle the mast with my arms straight, and begin to lift, and walk backwards. I can see shrouds and backstay to know if anything is mis-aligned or kinked. It's not such a bad lift, because the mast is almost 1/2 way up to start. Once up, it's easy to hold mast with left hand against swept uppers and backstay, and reach down with my right hand to pull the spin halyard tight and cleat it off in the cam cleat. Now the mast is standing full up, and I can go grab the forestay, pin it, tighten the turnbuckle.
I have in the past had to lower mid-hoist, and my bow roller at the top of the crutch is a bit narrow. I'd love it if it were twice as wide. Also, putting the tall crutch up is a PITA because of the reverse counter of the stern. At such time as my crutch wears out or breaks or something (maybe the wood will rot out? Please?) I will just buy one of these:
Mast Up Sailboat Mast Raising System I have spoken with the maker of these crutches, and they have designs that accommodate the reverse counter thus keeping the crutch completely vertical and not angled forward. They also have something to prevent the crutch pivoting on the gudgeons (as I have designed into mine.) Not sure if they make something with a wider roller than I used, but that's yet another detail.
Note I do this facing aft from the cabin top, because I have NEVER been able to face forward from the cockpit with the mast on my shoulder lifting up, feeling like I have good lateral stability. And there's no way I can step from a seat up onto the cabin top with the mast on my shoulder and not have it go off centerline and feel like I'm going to drop it over the side. But I am very secure straddling the mast facing aft and keeping it on the centerline. This is how I do it for a friend's Catalina 22 with much bigger mast, with him lifting from the cockpit until I can take over for the remainder of the hoist, and also keep it stabilized. We did not that stepping his mast seemed way harder this year than last year. We just assumed it's because we are 1 year more decrepit and older.
