Not sure if this would help, but I had a similar problem when I replaced the roof on my 150 year old house a couple years ago. The joists were swayback - like 3 inches in on a 16 foot plan and the sheathing rotted. So I had to remove all sheathing, sister the joists and put new plywoid sheathing. The edge of the roof is about 20 feet off the ground. I had scaffolding hardware they sell at the big box stores that use dubole 2x4 posts. I did this piecemail over the summer by myself occasionally with a helper, but more often alone.