Jared,
I have been asking myself the same question all summer. I don’t like sailing without the fly but am trying to muster the courage to go up there and fix it. I think it is a right of passage for a sailor to do that so that is one positive. It would be a first time and hopefully not the last time for this old fat man. It’s an intriguing question.
Brian
I’m pretty sure it’s within the boat’s limits if your concern is your weight.
If you feel you’re physically fit to do it, then it’s up to you.
I don’t know if by “winch myself to the top,” you mean, “all by myself.” If not, the following is for others to consider rather than directed at you.
I used to go up masts solo when I was younger. Big fan of the ATN TopClimber. Looking back, I now realize that it’d have been safer to have had someone with me. Even the best of us can make mistakes, and it’s nice to have someone around just in case.
My rethink of solo mast-climbing came when I was asked to donate to a GoFundMe campaign for the fall injuries sustained by the best-known rigger in my local area.