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If the roof is "interesting" at all, at a minimum, I will put brackets along the edge, andd maybe part-way up, and possibly at the work point, like below a chimney or skylight if I need to work and keep tools and materials right there. http://www.ajctools.com/brackets.html
Three or 4 of them, on 4' centers, nailed to rafters with 16d nails, with a good 2x6 run through, and they will take quite a load.
If it is steep, >10/12 and high, I choose between two alternatives, a harness anchored at the peak, or a hired roofer. At that point, I opt for the latter.
Extension ladder extend the ladder 3 ft or more past the edge of the roof. Make sure the ladder is secure and the base is the appropriate distance from the building.
If the roof is 20 ft high and you have the ladder at 23 ft minimum then you need to have the ladder at least 5 ft out from the contact point at the edge of the roof. 25 ft high would be 6.25 ft out or you can hire someone else.
It is not that hard once you are up there just keep your center of gravity low and pay attention to what you are doing and where you are. As long as you aren't deathly afraid of heights or suffer from vertigo.
The walking around part is a piece of cake on most roofs that do not require roof jacks and planked staging. On extremely steep roof(s) you cannot freely walk around. Number one is it not safe, number two you will tear up the roof in many cases with your feet.
For the more moderate pitches you just have to get used to the thrill of being on the roof. If you want to be technically correct, OSHA requires and many codes demand a staging be set to catch you if you should slip, fall or slide off the roof. Some places will let you get by if a safety rope is stretched across the entire gutter area of the roof. Lots of places assume you know what to do. Just the ladder up there is enough. If you fall it is your neck. You have to know when a roof requires it to be staged in some manner to get safe access.
Here is some general ways they might stage a roof. Generally you also use planks with roof jacks on steep sections.
If you don't know what you are doing or don't have the proper equipment / staging / knowledge, stay on the ground. Why do you want to get up on the roof?
I know ladders will get me there. I meant once I was on the roof. It would not be fun walking around without rope or something unless I am suicidal.
Is your name Tim Taylor?
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Get a ladder stabilizer
