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Wilson Roofing Blog — Hiring a Contractor

How to Choose the Right Roofing Contractor

Eight questions to ask before signing anything — and the red flags that should send you running.

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Tampa & Sarasota, FL

Article — 5 min read

Hiring a Roofer Shouldn't Be a Gamble

Florida's roofing industry has more than its share of fly-by-night operators. After a major storm event, out-of-state crews show up, sign easy contracts, take deposits, and disappear. Even in normal times, the gap between a great roofing contractor and a mediocre one can mean the difference between a 25-year roof and a roof that fails at year 12. Here's what we tell our friends and family to check before they hire anyone — including us.

1. Are they licensed in Florida?

Florida requires roofing contractors to hold either a Certified Roofing Contractor (CCC) license or a Registered Roofing Contractor (RC) license. Ask for the number, then verify it on the Florida DBPR website (myfloridalicense.com). If they can't or won't give you a number, walk away.

2. Do they carry workers' comp and liability insurance?

Ask for a certificate of insurance — not a screenshot, an actual COI. If a crew member gets hurt on your property and the contractor doesn't carry workers' comp, your homeowners' insurance can end up exposed. Liability coverage protects your home if a crew damages something.

3. Are they local — and how local?

"Local" can mean a lot of things. Ideally, you want a contractor with a physical office in the Tampa Bay or Sarasota area, a phone number that goes to a real person, and a track record of work in your specific area. Storm-chasing crews with out-of-state plates rarely come back to fix a problem two years later.

4. Will they put it in writing?

Verbal estimates are not estimates. A real proposal includes the scope of work, materials, manufacturer, fastener type, underlayment spec, deck repair allowance, total price, payment schedule, and warranty terms. If the proposal is one paragraph on a phone screen, ask for the real version.

5. What does the warranty actually cover?

There are two warranties on every roof: the manufacturer's material warranty and the contractor's workmanship warranty. Ask about both. A 50-year shingle warranty doesn't help you if the contractor goes out of business and the failure was caused by improper installation.

6. What's the deposit and payment schedule?

Florida law caps the maximum deposit a roofing contractor can take. Reasonable: a deposit at signing, a draw when materials are delivered, and the balance at completion. Unreasonable: 50% upfront, full payment before work starts, or "cash only, today only" pricing.

7. Can they show you recent local work?

A real contractor will gladly show you recent projects — addresses, drone photos, references you can call. If everything they show you is from another county or another state, that's worth questioning.

8. Do they pull permits?

Most jurisdictions in Tampa Bay and Sarasota require a permit for any roof replacement. A contractor who suggests skipping the permit to save money is a contractor who doesn't want their work inspected. That's a red flag the size of a billboard.

Bottom line: a good roofing contractor will answer all eight of these questions clearly, in writing, without getting defensive. If anyone bristles at being asked, you have your answer.

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