One of the toughest contractor jobs to hire someone for is roofing. This is because there often times are huge price differentials in quotes for jobs and the quality of the work is largely unknown until after. One thing you may want to do is go to a consumer site that rates contractors such as Checkbook.org. Other things you should do are:
- Get bids for any contract and compare prices amongst contractors
- Arrange to make payments in installments as the work completes that way the contractors have an incentive to get their work done timely (note although many roofers may not agree to it, but if you can try to negotiate to make the last payment after the first major storm)
- Get proof of contractor's license, liability insurance, and worker's comp insurance
- Write up contract specifics about what exactly the roofing job should entail (ie old shingles to be removed, debris removal, whether flashings or weatherproofing is to be replaced, materials and types to be used, and warranties)
- Get an estimate of time lines, who is going to be in charge, how many people will be working on the project, and materials to be used
- Get a warranty in writing from the roofer guaranteeing that the roof will be free of leaks for 5 or 10 years baring accidental damage to it
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