Re: Mast work
When I was much younger I worked as a rigger. We went up and down masts all the time... even commissioned a few C&C 36's back in the day. We would climb in the bosun's chair with a partner to tail the slack. Always with a few turns around a winch just in case.
To the OP, here are a few thoughts: It can be pretty intimidating up there the first couple of times. It takes more strength than you think and will tire you out. I would not make your wife try to winch you up.
For myself, when I got back into boating and decided to buy a sizable boat to live aboard, I knew I was gonna have to lose weight and get into shape. Just being aboard for a rough passage can wear your ass out!