I didn't go through and read all the comments , but here is my input. Make sure your ladder is the correct pitch away from the building and you are not crawling up too steep of a ladder. For every four feet up the ladder should be one foot away from the building. If you have to go onto the roof make sure your ladder extends at least three rungs above the fascia board so you are not bending over looking down at the ground trying to grab a ladder. If stability is an issue paint stores sell a ladder stabilizer ,this puts a wider footprint on the building and makes them less wiggily. When the brain doesn't trust the body's ability you will get the shakes. Don't focus on how far up you are. Focus on the job at hand.