Re: winching up the mast,
Get a 110v right angle power drill and a winch drill adapter. I've not done it myself, but seems like a cleaver idea.
The Cranker - a S.S. Sailboat Winch Drill Adapter Bit
Be absolutely sure to have a redundant halyard that the climber themselves can arrest an accidental descent. I like the prussic knot tied around a backup fixed halyard.
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In the harsh marine environment, something is always in need of repair. Margaritas fix everything.