certainteed has a line called "luxury" that has several shake look alikes to choose from. i think they look great. a little description from their website: "Presidential Shake TL Shingles - Color: Weathered Wood The luxury shingles with the look of cedar shakes and the performace of one of the finest composition roofing solutions in the industry. Presidential Shake TL gives your home the distinct look of a hand-split wood shake roof with the durability and performance that leaves wood in the sawdust. You get sculpted edges, staggered lines, and triple layer depth, for an amazing ground level effect that will last and last." heres the link: http://www.certainteed.com/products/roofing/residential/luxury

Cedar shakes are typically random widths not less than around 3" up to no more than 12" or so. They are typically around 5/16 - 3/8" thick at the butt end and narrow down to about a 1/16" at the non concealed edge. They are usually 16-18" in length. To make shingles out of flat stock, (your 1/2") would mean a whole lot of painstaking planing by hand to get that taper. If you are closer to the west coast, the shingles are typically redwood while on the east coast they are red or white cedar. Canada has distributors as well. You should probably do more research for suppliers and compare shipping costs.

So we did some more test painting and decided on the muted gray/blue for the main sections, similar to what gracie linked. We tried 2 different trim colors and are feeling like the dark gray blends in too much with the blue. The lighter gray seems to have more contrast. What does everyone think? Also, what would you recommend to paint the lower concrete section of the house. The lighter gray trim color if we pick that? Or would you possibly paint it a darker gray like the trim we weren't digging? Gray/Blue with light gray trim: Gray/Blue with dark gray trim (on right side of garage): Closer pic of Gray/Blue with darker trim: lighter trim in the shade: Close-up of lighter gray trim: (Middle of pic): Lighter gray trim again. Lower concrete section that will need to be painted:

Cedar shake roof are great...for about the first two years. Then they start to deteriorate and require lots of maintenance, and then repair. Cedar shake roofs from the 1950's and before lasted a long time because of the quality of the first-growth cedar. Now the shakes come from newer, faster-growing trees that don't have the same rot resistance. I had cedar shake roofing on a house I owned for 30 years, and vowed never again. The roof in your pictures looks like mine did before I started having leaks and needing roof replacement. There are techniques for replacing shakes with concealed nailing, but you can only keep putting bandaids on for so long. Those face-nailed shakes of yours are probably from an incompetent roofer who was replacing rotted out shakes. The tar paper showing through is another telltale sign that the roof is on life support. Plan on replacing it soon, preferably with something requiring less upkeep. The house I have now has steel roofing that I never have to clean and will outlast me.