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Yes, you need to contact a roofing company to check it out. Possibly need a rain diviter installed. Possibly need a gutter installation company to swap out current gutters for larger commercial size gutters.
Probably need to have the skylight reflashed. Skylights need to have special flashing kits designed for skylights. Have a professional come to inspect to see if you have a curb mount or deck mount skylight and they will be able to give you a price to replace your current flashing with a new airtight skylight flashing kit.
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