This seems like a no brainer, but you would be surprised how many people go with a risky roofer.
Let’s say that a worker falls off the roof and gets injured. It is important that there be workers’ comp insurance in place to pay for medical bills. Not only do workers need to be covered, but the job needs to be covered too. What happens if a contractor leaves the roof in a mess? You want them to pay for that, not you.
Also, is the company even licensed to do the roof? Not only should they have a business license, but they also need a state license. If the roofer isn’t licensed, there is a good chance he or she isn’t bonded and doesn’t have insurance. Dealing with insurance leads to the last point.