I would not advise anyone to do something dangerous, but just a few thoughts: 1) If time or money is an issue or you're just a compulsive do-it-yourselfer, one safety option is to hire a pro to install permanent fall arrest anchors at the roof ridges and on the wall of your house. This lets you do it yourself on the roof or ladders safely wearing fall arrest equipment. 2) I hired a painter once who painted the walls above the pitched roofs on my house using a little stepladder-looking device with adjustable legs, designed to provide a level surface for a longer ladder. I don't know if he made it or bought it, although it looked manufactured. Here's something similar: http://www.provisiontools.com/pivit/. Although that painter didn't use fall arrest gear, I'd recommend it for any ladder work over a few feet, and always on a roof. 3) In hurricane states like Florida after a hurricane, you'll have trouble getting your insurance company to respond, much less hiring someone to do anything to your house for at least a month. So your only option for replacing shingles that blow off or repairing (even temporarily) any damage is to get up there and do it yourself! 43) I agree that safety should always come first, but I have to wonder how one becomes a "ladder expert" if not by asking advice from people with experience . . . ? It's really not helpful if the answer is, "You can't get there from here" . . .