Not as hard as you think
Larry, recently repainted the mast of an '82 H-36. I had similar apprehensions. If you've never used roll and tip method, it's actually easier than it sounds.Here's what I did, and I apologize if I'm repeating anything you already know. I assume your mast is off the boat and off the ground. You will want to hold the mast off the ground from the ends - I used a 2x4 inserted in the bottom of the mast stepped on a ladder, and rested the masthead on another ladder step. This way I was able to get to the whole mast. I used Interlux Perfection two part expoxy paint. It's more expensive, but it's better quality.1. Removed all s/s hardware and bagged/tagged. IMPORTANT to do this when you put it all back together.2. I used 200grit wet or dry sandpaper to sand the complete mase and spreaders. Check for flaking and/or corrosion. Clean and re-prime these areas with two coats. Sand this area as well.3. Wash with water, and wipe down with clean towel, and let dry.4. Instructions provided by Interlux were right on. Need to be very careful about the ratios of paint and catalyst. Let it sit for 15 minutes and then add thinner.5. I started at the top of the mast and worked down. That way any mistakes would be harder to see. 6. I worked in 3' to 4' sections on one side of the mast at a time. I rolled on the paint with a thin foam roller fore and aft on the mast. Then I used a good quality 2" brush and very lightly stroked up and down the mast.7. After that section is done, I moved lower on the mast. I constantly looked back and underneath to make sure there were no drips and I also was careful about where sections joined. After a while you get the hang of it.8. I followed the instructions regarding sanding in between 2 more coats, and letting the paint dry at least 24 hours.The final result is beautiful, and the mast looks like new.BTW this is also a good time to rewire the mast.Good luck.Pete