hey brian my my name is Richard Calo. I own a successful contracting company in Cincinnati Ohio. first things first do not hire a handyman the fact that you already went up there and inspected it. Yourself was the best thing you could do the second thing you need to do is contact your home owners insurance and third thing you need to do is start looking for recommended companies roofing companies that are licensed paying for out-of-pocket you’re looking at a pretty penny depending on the size of your home and how old your shingles are. It sounds like you might need a replacement. I do not believe in patchwork, especially on the roof or any exterior work messes with the structure itself and the way shingles are laid to replace and repair diy I know it’s done and people have done it. I highly do not recommend it.