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I was out inspecting my roof today and found one corner that wasn't finished well. I took a pic: I'm tempted to squirt some black roof repair caulk into the hole under the shingles. The wood beam that is sticking out might be construction or it might be decorative. I'm not sure right...

My office room has a deck above, 12'x12', and is leaking on the side. The deck is finished with terra cotta tiles, plastic and other impermeable layers, but it leaks anyway. I'm going to have to rip up the deck and replace, plus redo the ceiling and walls inside to get rid of what ever is...