I need to extend as far as possible a 28' extension ladder onto a 10/12 pitch roof to change a HPS bulb every 3 years. So much for their 8 year warranty,
I run a heavy rope over the top of the roof and hook the ladder to a garden tractor on the other side to pull the ladder up all the way. The bottom of the ladder is inside a extended tractor bucket near the roofs edge to hold it steady. With the rope holding the ladder just in case the tractor moves I feel fairly comfortable to reach the peak while climbing on the laying down ladder.
I don't like it but you do what you can to get the job done. I thought about just putting in a light I can reach with an 8' step ladder and forgetting the high one.