That's a pretty apt description; you might find it easier to use an conventional extension ladder, you can raise the upper section once the ladder is against the structure.
Still, it's not easy for *anyone* if it's a sufficiently awkward location, or a high enough wind.
Many people - especially if they work construction - can be pretty casual about ladders, but they are killers.
A Home Inspector working in the next town over was killed a few years back by a fall of around 8'. Probably, as he drove up to the single story house, he was thinking 'Piece of Cake'. When I was a child one of my neighbors was electrocuted when his ladder touched a power line. This spring, two workers well killed in a fall a half-mile from my house.
I was "lucky" enough to have gone off a 2nd story roof as a young man without serious injury (patch of loose granules on a seemingly not very challenging roof - I went down through tree branches, breaking the fall), since then I've taken ladders and heights *very* seriously.
So my advice to ANYONE if they don't feel comfortable raising or using a ladder in a given situation is DON'T DO IT.
Find someone to assist you, or as much as you would like to do the work yourself, hire it out - whatever you are trying to do, it will be harder to do if you are dead.
Michael Thomas Paragon Home inspection, LLC Chicago, IL mdtATparagoninspectsDOTcom eight47=475-5668