Safely Paint On Garage Roof

I m worried about safety.
Safely paint on garage roof. So far we have figured out how to paint most of the house safely. We are looking for a lift or something to paint this last gable. Probably 36 40 feet high. Brush and sprayer extenders whether you re using a brush or an airless sprayer to paint the gable an extension tool can help you reach past the point your ladder will reach.
For spraying use a spray tip extender. The roof is sloped on both sides and the exterior that i need to paint is too high to reach without a ladder. My roofs are 5 12 so pretty easy to walk around on i get up there many times a year to blow out the gutters and sweep my chimney. Painting this section of your house that has a steep roof is impossible without a way to safely stay on it.
I do not like being on steep roofs and would probably not use this on anything steeper than 6 12. Bidding on a two story colonial style house that will require me to stand on roof over the garage. Purchase a brush extender which allows you to clip the brush securely to the end of an extension pole. The house is on a hillside and the driveway slopes downward.
Calling in the experts to paint exterior dormers on a 17 pitch roof. I do not paint many exteriors so i am kind of green when it comes to rigging up ladders scaffold etc.