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As a remodeler, one of the most popular types of additions I build is the shed dormer. Typically, a family will outgrow the limited upstairs space in a cape and will decide to raise the roof at the rear of the house. This increases the living space while still maintaining the look and feel of the cape in front. The trick in retrofitting a dormer is to get the roof off and back on as quickly as possible. I've built a lot of shed dormers and so far, I haven't had a problem with bad weather. A lot of this is luck, but part of the reason is that the approach I use guarantees that the roof will be off