The 10 Questions I Wish Every Homeowner Would Ask Me During an Estimate

Most people don't know the right questions to ask a roofing contractor, so they just look at the bottom number on the estimate. That's a mistake that costs Jacksonville homeowners thousands of dollars every year.

After 24 years in the roofing business, I've seen what happens when homeowners hire the wrong contractor. I've also seen the relief on people's faces when they realize they asked the right questions and avoided disaster.

Here are the 10 questions I wish every homeowner would ask during a roofing estimate,and what the answers should tell you.

Question 1: "Can I See Your Florida Roofing License?"

This should be automatic. Every legitimate Florida roofing contractor has a license number that starts with "CCC" (Certified) or "RC" (Registered). They should be able to provide it immediately,it's on their truck, their business card, and their contracts.

Red flags:

• "I'll get it to you later"
• "We work under another company's license"
• Any hesitation whatsoever

What to do: Verify the license at MyFloridaLicense.com. It takes 2 minutes and confirms they're legitimate and in good standing.

Question 2: "What's Your Workers' Compensation Policy Number?"

This is the question most homeowners forget,and it's critically important. If a worker gets hurt on your property and the contractor doesn't have workers' comp, guess who gets sued? You do.

Some contractors claim an "exemption" because they're owner-operators with no employees. This is legitimate under Florida law, but be cautious,if they bring any helpers, those workers need to be covered.

What to do: Ask for a Certificate of Insurance showing workers' comp coverage. Call the insurance company to verify it's current.

Question 3: "Who Will Actually Be Doing the Work?"

Some roofing companies are essentially brokers. The salesperson who gives you a quote works for the company, but the actual labor is subcontracted to whoever is available that week. This creates accountability problems.

What you want to hear:

• "Our own crews do the work"
• "We use the same team on every job"
• Specific names of foremen or crew leaders

What's concerning: "We work with several different crews depending on availability." This often means inconsistent quality.

Question 4: "What Happens if It Rains During the Job?"

This is Florida. Afternoon thunderstorms are a daily occurrence from June through September. A professional contractor has a plan for this.

Good answers include:

• "We monitor weather closely and plan tear-off timing accordingly"
• "We have tarps ready and can cover any exposed areas within minutes"
• "We never tear off more than we can seal or cover in a day"

Bad answer: Shrugging or "we'll figure it out." Your home shouldn't be an experiment.

Question 5: "What's Included in the Price,and What's Not?"

The cheapest quote often becomes the most expensive project when add-ons start piling up. Make sure you understand exactly what's included.

Ask specifically about:

• Tear-off: Is full removal included, or are they going over existing shingles?
• Sheathing/decking: What's the price per sheet if wood needs replacing?
• Drip edge: Will new drip edge be installed?
• Underlayment: What type? Synthetic or felt?
• Flashing: Is new flashing included at all penetrations?
• Permits: Are permit costs included?
• Cleanup: Who handles debris removal?

A detailed quote that itemizes everything is a sign of a professional operation. A vague "roof replacement: $X" should raise questions.

Question 6: "Can You Walk Me Through the Installation Process?"

A knowledgeable contractor should be able to explain exactly how they'll install your roof,step by step. This isn't to test them; it's to ensure they actually know what they're doing and follow best practices.

Listen for:

• Proper underlayment installation technique
• Starter strip and drip edge placement
• Valley and flashing details
• Ventilation considerations
• Manufacturer specifications

If they can't explain the process clearly, they probably shouldn't be doing the work.

Question 7: "What Warranties Do I Get?"

There are two types of warranties on a roof: manufacturer warranty (on materials) and workmanship warranty (on labor). You need both.

Ask:

• What's the manufacturer warranty length?
• Is it prorated or non-prorated?
• What's your workmanship warranty?
• What does it cover specifically?
• How do I make a claim?

Be wary of extremely long workmanship warranties from new companies. A 25-year workmanship warranty means nothing if the company doesn't exist in 5 years.

Question 8: "How Long Have You Been in Business Locally?"

Roofing has low barriers to entry. After every hurricane season, new "roofing companies" pop up to capture the demand, then disappear when warranty claims come in.

What you're looking for:

• Established local presence (5+ years minimum)
• Physical office or yard in Jacksonville
• Track record of completed projects in the area
• References you can actually contact

A company that's been in Jacksonville for 10+ years has weather multiple economic cycles and hurricane seasons. They'll likely be here when you need them.

Question 9: "Do You Pull Permits?"

In Jacksonville, roof replacement requires a permit. This isn't bureaucracy,it ensures the work is inspected and meets code. The permit should be in the contractor's name, not yours.

Why this matters:

• Unpermitted work can void your insurance
• It creates problems when you sell
• You have no recourse if work doesn't meet code
• The contractor may be unlicensed (only licensed contractors can pull permits)

Red flag: "We don't really need a permit for this" or "You can pull the permit yourself." Walk away.

Question 10: "Can I See a Written Contract Before You Start?"

Florida law requires written contracts for home improvement work over $2,500. But beyond legal requirements, a good contract protects both parties.

The contract should include:

• Complete scope of work
• Material specifications
• Total price with payment schedule
• Estimated start and completion dates
• Warranty information
• Permit responsibilities
• Change order procedures
• Dispute resolution process

Never sign a contract with blank spaces or vague language. If something isn't clear, ask before signing.

Bonus: Trust Your Instincts

Beyond these specific questions, pay attention to how the contractor makes you feel. Are they patient with your questions? Do they explain things clearly? Do they pressure you to sign immediately? Do they show up when they say they will?

A roofing project is a significant investment, and you'll be working with this company for at least a few days. Trust matters.

Get a No-Pressure Estimate

At Gimo's Roofing, we welcome these questions, and we're happy to answer them in detail. As a trusted roofing contractor in Jacksonville, we've been serving the community for over 24 years because we believe in doing things right.

Whether you need a roof replacement or roof repair, we provide honest assessments and transparent pricing. Call (904) 606-5313 for a free estimate and put us to the test.

Before you call anyone, make sure you know how to verify their Florida roofing license.

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