Re: Going up the mast
If you use a climbing harness make sure to add leg loops that you can use to support your legs. Most climbing harnesses are designed to be used when the legs are active and can cut off blood flow if used in more of a sitting position. The leg loops can be simple, even two pieces of line with a bowline in the end for your foot will do the job.
My friends and I used to haul each other up the mast, but it is a lot of work winching someone up there, even if you add a second block and tackle and use a big winch handle. We've since switched to using a ATN Mast Climber (similar to the system of ascenders that James uses) and it's a whole lot easier. We still like to have a second person on the boat following with a redundant halyard on a winch just in case something goes wrong with the climbing gear.
The Mast Climber isn't cheap, but it turns out to not be that much more expensive than buying a simple bosun's chair and the climbing hardware. I got my Mast Climber for about $350 on eBay.
boats that I sail on regularly: Pearson 28-2, Rondar 505, Yankee 30, Blanchard Junior