Shingles as siding?

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Who's going to be doing the roofing?
Main reason I ask is there's a special nailing pattern when doing that style roof with dimensional shingles.
There made with two layers of material, nail them in the wrong place or not use enough nails there going to come apart and start sliding down the roof.
I've seen it way to many times.

Special nailing and hand sealed with roofing cement. Nails should ALWAYS be placed in the nail line reguardless of roof pitch, extra fastners are required for steep slope.

My buddies and I will be doing it.

Please tell me more about how to do the steep part.
 
Will you be doing the roof too or just the upper walls.
This will also be a good time to check for needed work around the windows too.

I need to do the roof. The upper walls are curling. The lower walls, the paint is pealing off the metal siding.
Everything is being done.
 
Except for the lack of roof overhang(eve) that is the same house as next door with no shingles on the second level.
 
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