When we were looking at this house to purchase, a major concern of ours were the roofs of the house and the barns. All the buildings on the property had cedar shake on them and while they looked rustic and charming, they were also clearly in trouble. You could see daylight from inside the house (typically cedar shake does not have underlayment) and there were obvious signs of former leaks. Moss was also growing rampantly on the roof, especially where trees were keeping it shaded. All of this to say, we knew going in that one of the first things we would need to do would be to replace the roof.
The question was what to replace it with? We both felt that we could not replace it with asphalt shingles. There is not a thing wrong with asphalt shingles, all of our other houses had them, but it just didn't feel right with a house of this age. We seriously looked into using cedar again but, unfortunately, we were given the advice over and over again that cedar just isn't the same as it used to be (no more old growth!) and that we would probably have a lot of upkeep and might have to replace it in 15 years! So that was a no go.
In our area, you often see beautiful slate on old homes. Unfortunately, it didn't make financial sense to put slate on the house, but our roofer introduced us to engineered slate (fake slate). At first, I was adamantly opposed to using any material that wasn't real. However, our roofer had us go look at other homes that had used the product and I was impressed with how great they looked. So after research and discussion and field trips and more discussion, we ended up using the product. Now that it's done, it looks really lovely and beautiful.
It feels good to get such a major thing done and accomplished. We are trying to work on the basic foundation type of issues with the house, after all what's the point of a new kitchen if your roof doesn't keep water out?