Here's the lastest update. The shingles provided for this structure were very nice, Cedar Shake shingles made by Northeastern Scale Models. There are three sheets in the kit and that's more than enough to complete the roof on this stucture. I first stained them with a light A&I wash and let them dry. Prior to gluing the cardstock roof in place I took a pencil and a square and drew some horizontal lines on the unprinted side of the roof. I also marked and scribed the the unprinted side to fold the roof. I did this so the printed side, with the guidelines for the rafters and rafter tails, would be underneath instead of on top. I've already glued all of those in place and applied 3M Transfer Tape to the top of the roof. When I applied the shingles I opted to add just a thin line of Canopy glue to the top of each row prior to attaching the row above. I probably didn't need to do that, the 3M Transfer Tape should have more than enough bite but I did it anyway.
After I covered the exposed portion of the 3M Transfer Tape with shingles I then trimmed the shingles to size using an X-Acto knife with a chisel blade in it. These are real wood shingles so it takes a sharp blade and a little bit of pressure to trim them.
After the roof was finished (except for some final coloring with powders which I'll do later on) I added the small entry way to the wood structure. Two walls and roof.
Here's how the wood structure will be positioned with regards to the brick structure. There's a small wood structure that will cover most of this brick wall as well. Unfortunately I'll probably have to remove the sign on the brick wall. I think the roof of the small structure will obscure part of it.
More to come as I make progress.