This mast step idea might help.... maybe even think of rigging up a pulley system from the mast to the stem head to raise and lower the mast. Maybe? Might work.
Originally Posted by Wayne Jeffers
Anyone who has attempted to lift an 18 foot mast into or out of the common small boat thwart and step, in a breeze of wind, knows it is a most precarious operation requiring strength and agility of no mean order. The Maryland Eastern Shoreman took a dim view of such strenuous pastimes so he devised a simple, effective solution. First, the mast thwart: this was placed so its after edge, hollowed out in a half-circle, came to the mast centerline when stepped. The mast was secured by a "clamp"; strap iron shaped as shown in the plan, secured by two staples made of rod driven into the thwart's after edge. These staples would be 1/4-inch iron rod in this skiff and would be driven into the thwart about 4 or 5 inches; suitable pilot holes are bored for each leg. The clamp was slotted, passing over these eyes and held there by iron or hardwood pins or wedges.
Eastern Shore mast step and clamp.
This clamp business left the fisherman with the problem of getting the heel into the step. The Marylander solved this by a simple design; the step was made of two fore-and-aft plank chocks, each bolted to the bottom through the keelson, and just far enough apart athwartships to allow the mast heel to fit snugly between them. Through these chocks an iron rod was driven athwartships -- near the top of the chocks -- as shown in the plans. Now, the mast heel was slotted athwartships to fit snugly over the pin. Well, to step the mast, you placed the heel of the mast between the chocks with the slot over the rod and then walked the mast up until it came home in the thwart -- after which you put the clamp into place, holding the mast in position by one shoulder. To lower the mast you reversed the process, with everything under control. It was all very simple.