My boat is not too much smaller than yours. Stepping and unstepping the mast isn't trivial, but it's not hard when prepped.
My technique has evolved. Key to this is a crutch made from an 8' 2x4 with roller at the top, and "pintles" fashioned from a square U bolt cut in half to create L pintles. These fit into the gudgeons mounted on the back of the boat. It is difficult to go from the storage and travel crutch which holds the mast on the centerline, to the mast propped up on this tall crutch. The key to this is that the tall crutch has already lifted the mast to about 40º, which is the worst part of the lift or lower.
I stand on the cabin straddling the mast, facing aft. I can lift the mast from this high crutch position very easily, and I can easily see what the standing rigging is doing. Usually, the backstay kinks up the triangle plate for mainsheet attachment. This year I split some vinyl tubing to put over the triangle plate area, and it held the backstay straight so no kinking. The lower and upper shroud turnbuckles usually stay well upright if I place them in that position, but if I see one fall over, implying a bent stud may occur, I can lower the mast into the crutch and prepare again. Also, I have a few cleats on the sides of the house for asym tack line, and jib downhaul line, and I occasionally get something hooked there. Again, it's very easy to glance side to side quickly and catch these problems early on.
Lowering the mast would be much easier if I had a 6" or wider roller at the top of my crutch. It would be a bigger target to aim for. There is a company on the West Coast that makes a metal crutch, with sections that slide inside each other. It's designed for trailering, and to easily raise the mast up to my critical height, but I think it costs $250. If I had a welder and I hung out at metal supply companies, I know it would be quite easy to fabricate my own, but being a woodworker and not much of a metalworker, I make do fine with what I've got.
If you need pics, let me know, I have them at home.
Another way to make mast stepping and unstepping is to rig a gin pole, and some form of baby stays to hold the mast straight during the hoist. I think I'd also use a long crutch. The key to baby stays is to make SURE they pivot at the exact same point as the mast step hinge, otherwise they will be loose and won't hold the mast straight the whole way. I imagine a bridle rigged between stanchions, terminating at a welded ring at the pivot point, and then the stay going up the mast from there. Some people use winches on the gin pole, some use mainsheet purchase from the stemhead fitting, some people use an extension of the trailer winch stand (like Precision Boatworks does for factory supplied trailers on Precision boats.) There are loads of videos on YouTube, posts here, and Google searches that can show you many options. I haven't rigged anything yet, because I still feel young and strong enough to man up the mast myself.
Other people start the hoist in the cockpit, then somehow step up onto the house and lift it the rest of the way all facing forward. I don't know how the hell they do that; as soon as I try to step up, everything goes off the centerline, and that is NOT what you want to have happen.