Have you done this yet? How did it go?
If not: I have an H23, which must have a roughly similar size mast. I have only had this boat since April 2010, so I've done two cycles of stepping and unstepping, with one painful lesson. In 2010, when unstepping at end of season, my helpers from the yard did not steady it sideways properly, and at about 45 degrees, it swayed sideways and snapped the aluminum plate off the bottom of the mast. Luckily only the aluminum rivets broke (the mast tube needed a little unbending), so it was a fairly easy and cheap fix - just pop riveted it back on.
1. Don't try it forward - the length of the mast ahead of the bow pulpit and its weight/leverage would be very hard to handle, unless somehow you can have helpers in front of the bow, and they can reach high enough - tough if it is on a trailer or cradle.
2. Think about building a gin pole or A-frame type support, rather than trying to use a line like a sheet directly from the top of the mast. There are some good photos in the owner mods section of the H23's, and likely in other models. I found a good video showing the A-frame approach on an H23
here. I happen to use a fairly thick walled aluminum tube as a gin pole, only because my prior owner had built one. That A-frame made from conduit looks attractive, as it adds some lateral support.
3. I use a line with a double-block system (two blocks, each with two sheaves) to raise or lower it. That's, what, 4 to 1 advantage? It works fine, using one of the jib winches to pull it up or control it on the downward side.
4. To lower it this season, I built a pair of wood supports for side baby stays - that helped a lot. There are various designs for these baby stays. I used a loop of chain around the mast, pulled up to the spreaders with the main sheet. The stainless cable stays attach to the chain loop with shackles. The wood supports sit against the molded in toerail (the 23 lacks a metal rail with holes), held down tight to the deck with nylon straps with ratchets, under the hull. The wood supports are the right height so the eye bolts at the top are on a level with the mast step - the lower end of the stays has to be level to the mast pivot or else they tighten or loosen as you lower it. They don't have to be really tight (like say the "real" sidestays) as they are only there to help prevent the mast going too far side to side as it angles down.
5. It really helps to have the crutch at the stern extendable, so it is high enough to support the mast before it is near horizontal, and then can be lowered to the right height for storage. I added a wood plank extender to my metal crutch, and added a rubber trailer roller (the kind shaped like a sewing thread wood core) so I could roll the mast base forward more easily.