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Roof leak

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About two years ago we had a porch and a roof installed on our house. We used a contractor who did the porch and subcontracted the roof. We put a 40-year shingle on our roof. A couple of months after the roof was installed the roof around the skylight (which was installed a year before) started to leak. We called the contractor who came back (not promptly) several times to fix the problem. After trying several things to fix the leak, he told us that we had the wrong flashing on the skylight and if we paid for the flashing he would install it and repair all the damaged sheet rock for free. We agreed. A couple of months later the roof leaked again. He came back again doing different things that never resolved the problem. Finally after two years of it raining in my house, I called several roofers to give me estimates on fixing the leak. Most of them said that the 40-year shingle should never have been put on a low pitch roof. They suggested putting a rubber roof. We hired a roofer and paid $1600 to put on a rubber roof.

We figured we were done with the original contractor but today we got a call from him stating that he wants his money for the flashing. He had originally stated that we should put on a rubber roof but his only reason was because it would save us money. He never told us that our roof would leak if we put on this type of roof. Who in his or her right mind would put a roof on that someone says will leak? He is also now saying that he told us that it might leak. We had never planned on suing him or the original roofer but now we feel that if we do not pay him he will sue us. Do you think that if he sues us we will have to pay him the money for the flashing? We are also worried that if we do not pay him he will sue us for more than the price of the flashing $350.00. We assume he will add in time for labor and supplies and we may end up paying him a lot of money. In addition should we sue the original roofer and do you think we will win in small claims court? New york

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