I used to have a very similar house plan. Unless you have a really long extension ladder, it is a pain in the ass to get up there.
What I did is use my regular extension ladder to get on the roof of the garage. Next nail a 2x4 kick plate to your garage roof. Pull up your extension ladder onto the garage roof and set it up against the kick plate and proceed onto your 2nd story roof.
You'll need a couple dabs of blackjack roofing cement to patch up the 2 small holes in your shingles from nailing up the kick plate.
Good luck
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