How to Choose a Roofing Contractor: 2026 Checklist & Red Flags

By the Orlando Roof Inspection team · Updated October 2026 · 9 min read

To choose a roofing contractor, verify their license and insurance directly with the issuing authority, get at least three written line-item estimates, check the workmanship warranty in writing, and walk away from anyone who knocks on your door after a storm demanding a fast signature or a large upfront payment. A roof is one of the biggest repairs you'll ever pay for, and the right vetting takes an afternoon. Here's the checklist.

1. Verify the license

Don't take a license number on faith — look it up. Most states license roofing contractors, and you can confirm the number on the state board's website. In Florida, roofing contractors must be licensed through the Department of Business and Professional Regulation (DBPR), so you can check any Orlando roofer's status and complaint history there. A few states have no statewide roofing license, in which case check your city or county rules. Source: state contractor licensing boards; Florida DBPR.

2. Confirm the insurance

Ask for a certificate of insurance showing both general liability and workers' compensation, then call the insurer listed to confirm it's active. This matters: if an uninsured worker is hurt on your roof, you can be liable. Fraudulent or expired certificates are common after big storms, so the phone call is worth five minutes. Source: industry hiring guidance.

3. Get three written estimates

Three itemized bids give you a real baseline and expose outliers. Each estimate should break down materials, labor, timeline, permits, cleanup, and property protection. A verbal quote or a number scrawled on the back of a flyer is not an estimate. A bid that's dramatically lower than the others usually means thinner materials, skipped steps, or a change order coming later. Source: industry estimate guidance.

4. Check the warranty

There are two kinds, and you want both spelled out. The manufacturer's warranty covers the materials; the contractor's workmanship warranty covers the installation. Ask whether the workmanship warranty is a full warranty or an "up to" warranty, how long it runs (5–10 years is a reasonable minimum), whether it transfers to a new owner, and what's excluded. Get it in writing — a verbal warranty is worth nothing if the contractor disappears. Source: industry warranty guidance.

5. Understand the payment terms

A reasonable structure is a 10–30% deposit with the balance due on completion, or milestone payments written into the contract. Be cautious of a demand for more than half upfront, full payment before work starts, or cash only — cash leaves no paper trail. Everything, including the payment schedule, belongs in a signed written contract.

6. Red flags and storm-chaser scams

After every major storm, out-of-town "storm chasers" flood the area. Decline anyone who shows these signs:

A good move after storm damage is to get your own independent storm damage inspection first, so you know the real scope before any contractor quotes it. Sources: SouthwestExteriors; SquareDash; state consumer-protection guidance.

7. Questions to ask before you sign

• Are you licensed in this state, and what's your license number?
• Can I see your liability and workers' comp certificates?
• Who pulls the permit? (It should be the contractor, not you.)
• Is this a line-item written estimate, and does it include tear-off and decking repairs?
• What workmanship warranty do you offer, in writing, and does it transfer?
• Will you be using your own crews or subcontractors?
• Can you share recent local references and manufacturer certifications?
• What's the payment schedule, and what happens if hidden damage is found?

Sources

• Florida DBPR — Verify a contractor license
• Southwest Exteriors — Choosing a Roofing Contractor: Red Flags
• SquareDash — Roofing Contractor Red Flags & Scams