How long has the company been in business? Have they always been in business with the same name? Does the company have a street address (and an office), not just a post office box? How long have they been in business at their current location? Ask for references and check them. You might also check into other sources of information – like the Better Business Bureau or the local Chamber of Commerce.
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Did they do a comprehensive analysis of your roof and actually inspect every portion of the roof (some companies only look at a “sampling” and use that to calculate their bid)

Worker’s Compensation Coverage – protects you in case a worker is injured while performing work on your property.

General Liability Insurance – protects your property while work is in progress.

Completed Operations Insurance – a rider on a general liability policy that covers many problems that might occur after a job is complete.

Find a contractor that utilizes an additional level of supervision to oversee the foreman and crew.

Minimal or no insurance coverage.

Poor, unsupervised workmanship.

Low grade materials.

Not replacing current flashings.

Leaving you uninformed about problems that should be addressed.

Inadequate ventilation proposed.

Be sure all materials and work are specified.

Be sure the price is specified and firm, and that sales tax is included.

Payments prior to completion are generally not required for roof replacements. An exception may be required if non-standard materials are specified.