How to reach hard-to-reach area on roof

I'm a handyman w/o a lot of experience on roofs...work alone, and need help,THX! I am starting to install a leaf guard product on gutters. I have a prospect with a house where the pitches on the roofs are pretty steep and the 2nd story roof hips into the 1st story. The 2nd story has gutters that I need to install on. I can put a ladder on the 1st level roof with a roof hook and climb up to stand on the ladder and reach about 7' of gutter(the pitch is too steep to use a ladder on the roof)...as I work down the ladder, and then there is about 8' of gutter left that I can't reach, and a ladder from the ground can't get me over there beacuse the end of the 1st story roof stops me. Is it possible to get the ground ladder as close as I can....put on a ladder jack and then drop a walk board on it and the other end of the walk board directly on top of the roof. Or? is the walk board not supposed to lay directly on the roof? Stability of the walk board being the issue. Should I somehow attach the one end of the walk board(on the roof) to the ladder that I have on the roof(w roof hook)? Is there such an attachment(or tie it off), or better to lay it directly on roof? I also thought of installing a roof anchor and attaching to the top of the ground ladder so the ladder wouldn't slide sideways(for extra safety). Maybe there is a better way to skin this cat...so I thought I'd ask for some help. Thx

 

File:Lift Table Wheeled Extenders.jpg - Wikipedia, the free encyclopedia

Rent one of those.

 

Let me start by saying that I'm may not be qualified to give advice. I can't visualize exactly the situation you're describing but I thought I would offer something that has helped me in the past. I made a panel to set on my porch roof so that I could put another ladder on it to reach the second story roof. I took a piece of 1/2" plywood about 3' square and generously stapled heavy, fibrous carpet underlayment to one side. I lay this side down on the shingled roof and attached a cleat to the top side with screws from the bottom side. The screws sink through the soft underlayment so they won't damage the roof. Anyway, I attached a cleat to put the feet of my ladder against but you could build anything onto the platform to support a walking board or a ladder or whathaveyou. When I lay that panel down on the roof, it sticks, and feels really secure. Just a thought.