A cedar shake roof is a bit tedious, but it well worth doing, and not as hard as it looks.
I cut the shakes en masse to begin with. Each course is about an inch long. To make life easier, I first cut one-inch swaths across the grain of a wide piece of 1/32" balsa.
I then snap the pieces off to make rectangular shakes.
I lay the shakes down in courses. The shakes should run about a quarter of an inch off all edges--you can trim them back later if one side needs to be flush with a wall. I run a bead of glue in two lines for each course: one line where the bottom of the shake will meet the previous course, and one where the top of the shake meets the roof. When all the courses are complete, you can trim out the ridgeline with shakes running the other direction.
Cut a piece of Masonite hardboard and hot-glue the model to it. I usually do this before building the porch, which makes assembly a bit easier.
Paint your building dark sepia, they dry-brush it up to the desired color. For natural wood, this takes some experimentation with various shades of brown and tan to find the effect you're looking for. I opted for a very weathered look, however you might want a young town with brighter wood.
Good luck and if you have a question, feel free to drop me a line at email@example.com.