Re: Mast work
I would highly recommend you higher a rigger to do the work. You health and safety is worth the price. And you would not want to endager and inexperienced kid to do your work.
I work in rigging and weight handling equipment (which is what all of our running lines should be considered on a boat) is totally different than equipment used to hoist personnel. Although most of us get away with using this weight handling equipment to hoist people, many of us just "get lucky" at not getting hurt, and the rest may have enough experience to inspect somthing and make a good call as to if the equipment is safe enough to hoist a person, and to have enough back-ups in case of a primary failure.
What if you do get someone to hoist you up the mast and the winch fails or slips, what are your secondary supports and how will you get down. Just hanging in your bosuns chair for and extended period can effect your circulation and could cause a heart attack.