Get many quotes like 4 or 5 not just 2 or 3 and when you find the best one make sure they are licensed and insured so you can remedy any problems in the future.
Also its a good idea to get multiple quotes, do research, and ask questions. Much like buying a car.
You can definitely get a cheaper roof, but it's very easy to end up with a crappy roof that can cause major issues in the future. The house we bought had a very new roof on it but it had so many problems that we had to replace it, including leaks and rot. Your dad may be spending a lot on a roof, but he'll be getting a good one from Legit.
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