Here's a picture from last weekend. We took out the window in the bathroom to inspect the frame of the window. We wanted to check the exact size of the opening, and see how square it is. It's a little more than 1/4" out of square, so sash replacements aren't going to work without fixing the squareness. You can see some of the shingles I removed below the window. The house was insulated and had stucco over the shingles as well. So at every stud bay, there's a hole in the shingles.
We bought a box of cedar shingles. We went for the grade A cedar, pre-primed ones. They come in a box that says it covers around 50 sq. ft. with a 7" exposure. We have a 5 1/2" exposure, so it would be less on ours, maybe 40 sq. ft.. I primed the shingles that we're exposed, with an oil based primer. It probably wasn't necessary, but it wasn't much extra effort.
Here's a picture of the top corner. I had to remove quite a few shingles here. It`s difficult to remove just one shingle, even with a shingle ripper. At least we don`t have to remove the whole wall. The new shingles are actually longer and thicker than the original ones. I was surprised, I didn't think they`d be thicker. I know the old ones probably have shrunk though. You`re supposed to leave a 1/8" to 1/4" gap between shingles, I left around 1/8" or slightly less, 1/4" just seems so wide, and the originals seem to have hardly any gap. Hopefully they don't buckle. I think we'll be okay though. I used a utility knife to split the shingles, a handsaw for crosscuts, and a block plane to trim off a little bit.
Seth gives them a good knock, to make sure they're okay. I still have to finish the top row. There's a large section that we don't have to fix, because we're putting in french doors. More to come on that soon.