Check the Home Improvement Contractor licence yourself
Residential home improvement work in New York City requires a Home Improvement Contractor licence issued by the Department of Consumer and Worker Protection. DCWP publishes a licence lookup, so you can confirm a number against the business name before any money changes hands.
This matters beyond compliance. An unlicensed home improvement contractor in New York generally cannot enforce the contract or sue to collect - which sounds like your advantage until you need them to come back and fix something.
Insurance: ask for the certificate, not the assurance
You want general liability and workers' compensation, evidenced by a certificate of insurance issued by the insurer, not a photocopy the contractor keeps in the van. If workers will be on your roof, workers' compensation is the coverage that protects you if someone is injured.
For co-op and condo buildings, management will usually require the building named as additional insured before work starts. Request that certificate early; it is a common source of delay.
Which roof work needs a DOB permit
Straightforward repairs and like-for-like reroofing often proceed without a permit, while structural work, changes to the roof deck, and work touching means of egress or fire-rated assemblies generally require one from the Department of Buildings.
The contractor pulls the permit, not you. A contractor who suggests skipping a required permit to save time is telling you how they handle everything else.
Get the scope in writing before work starts
A usable proposal names the membrane or shingle system and manufacturer, states how many layers come off, specifies flashing and drainage detail, and sets out the workmanship warranty term separately from the manufacturer's product warranty.
Quotes that cannot be compared line by line usually cannot be compared at all.
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