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You mentioned not being able to get a grip on the line to help pull yourself up. I haul a fellow memer of our club up the mast whenever I need masthead work done. There's very little grinding of winch going on, mostly tailing. From standing on the boom, he's able to reach out and grab onto the lower shrouds. Since they angle out toward the bottom, he's able to get a good grip to help pull himself up, feet on the mast. When he reaches the spreaders, I have to pull him up the next couple of feet. Once on the spreaders, he can reach the upper shrouds and we repeat the process. I have to work pretty fast to keep both the primary and safety lines tailed, but it goes rather fast. At the top, I have to winch him up the last couple of feet.
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