Dave...
Going aloft is one of the few tasks where you really need to locate someone who has a little knowledge on the subject to give you a hand. My wife and I do this with no problem, she weighs in at 104 and I tip the scales around 200, she operates the winch. First do not clip the bosun chair with the hardware that is used to clip to the sail! Run the line thru and get back to the un-spliced section and use a safe knot, there are many, then clip on as a secondary with the hardware. The person on the winch does not have to hoist the man going aloft from deck to masthead by cranking, in reality the winch is only used to stop and hold to allow the man in the chair to lift himself a little at a time. If you think about it unless he is 4 feet tall when standing on the boom on your boat your almost halfway to the spreaders already. Use the shrouds to lift a bit while the person on the winch tails, take your time, 5-6 strokes and you can pull your self to the spreaders. It gets easier as the shrouds get closer to the mast. If your boat has 2 sets of spreaders even easier. On a larger boat it would require some winching to get started because the man going aloft would not be able to reach the shrouds at first. If possible always have 2 people on the winch.