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Thanks man.Welcome to BYC. If you add your location to your profile people will always be better able to give you targeted advice for your climate.
Here is my article on coop ventilation: https://www.backyardchickens.com/articles/repecka-illustrates-coop-ventilation.77659/
I'd take BIG rectangles out as high up as possible, think square feet rather than square inches, and put awnings over them to keep the weather out.![]()
On that I would likely cut out a triangle to match the profile, just make sure there's enough roof overhang to keep the rain out. Otherwise, I'd be using a ~4" hole saw and making multiple round holes under the eaves.
And more specifically for gambrel roofs.If there isn't enough roof overhang -- and most sheds don't have it -- here's how to extend the roof.
Here's how-to (and how not to), extend a roof by sistering the extension to the rafters: https://strousehomeinspections.com/blog/structural-roof-extensions.html
And here is how to use lookouts to extend the roof at right-angles to the rafters: https://www.backyardchickens.com/ar...e-overhangs-eaves-of-a-shed-coop-house.76599/