Leaking roof. help!
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Yes, You have to start again, this a time using material that will stand up to the weather. Plywood, fit Skylight, then Roofing Felt, using a waterproof sealant around your Skylight. Otherwise use Clear Polycarbonate Sheeting.
A good roofer will be able to repair the damaged area only. The trick will be matching the shingles if no longer available. You may need a new skylight too in the process. This happened to me 3 houses ago, but we were able to feather in the new shingles with the old successfully.
You are better off to redo the damaged area with plywood. Particle board will always be a problem around water....and since skylights tend to hold water around the edges, I think it will cause you problems.
Naomie is right on this one. Hire a good roofing contractor and he ca repair it withou s full rebuild. As far as the skylights go if they are faulty then replacing them is key to preventing further issues. Good luck