This one kicked my Azz..20 foot from ground to gutters for most of the house up down up down, move through the landscaping, through the trees. It was one of the first ones I did when I got into this business so it was a little challenging but got it done. It was great, I needed something...ring the door bell and ask the Butler..LOL
I would want adjustable ladder feet on those tall ladders your using and a standoff as well. You can reach over the gutter with a standoff and set it on the roof. This way the ladder is less prone to side to side movement. In that one picture your aluminum ladder had a pretty good angle to it that could crimp the gutter as well. The standoff would solve that problem.