Look, I'm gonna be straight with you. After 18 years in this business, I've seen good contractors and I've seen absolute nightmares. The difference between the two can mean $15,000 in your pocket or $15,000 down the drain. Worse, a bad roofer can leave you with leaks, voided warranties, and enough stress to last a lifetime.
Last month, I got a call from a homeowner in Ohio who hired the "cheapest estimate" for her roof. Three months later, water was pouring into her living room. The contractor? Gone. Disconnected number. No license on file with the state. She ended up paying twice—once for the botched job, once to fix it right.
Don't be that person. Here's exactly what to ask before you hand over a dime.
The 10 Questions Every Homeowner Must Ask
Question #1: "Are you licensed and insured in this state?"
This isn't small talk—it's protection. A license means they've met minimum state requirements. Insurance means if a worker falls off your roof, YOU aren't getting sued.
What to do: Ask for their license number and verify it on your state's contractor board website. Request a Certificate of Insurance and call the insurance company directly to confirm it's active.
Question #2: "How long have you been in business under this name?"
Here's a trick bad contractors use: they screw up, go bankrupt, and reopen next month under a new name. Look for at least 5 years under the SAME business name.
Red flag: "We've been doing roofing for 20 years" but the company was registered 6 months ago. Different story.
Question #3: "Can I see 3 recent references with photos?"
Anyone can show you a beautiful roof from 2015. You want to see work from the last 6 months. Call those references. Ask: "Would you hire them again? Any surprises?"
Question #4: "Who will actually be on my roof?"
Some contractors subcontract everything. That's not automatically bad, but you need to know WHO is doing the work and if THEY are insured. I've seen cases where the main contractor had insurance but the sub-crew didn't.
Question #5: "What's included in the written estimate?"
Get it in writing. Every. Single. Thing. Tear-off included? Dump fees? Drip edge? Flashing? Ice and water shield? Permits? If it's not on paper, it doesn't exist.
Question #6: "What warranty do I get—and from whom?"
There are two warranties: manufacturer's (on materials) and workmanship (on labor). The manufacturer warranty means nothing if the install was botched. Make sure you get at least 5-10 years on workmanship IN WRITING.
Question #7: "How do you handle unexpected damage?"
Once they tear off your old roof, they might find rotted decking. How is that priced? Per sheet? Per square foot? Get the price BEFORE they start, not while you're standing in the rain with no roof.
Question #8: "What's your payment schedule?"
Standard is 30-50% deposit, balance on completion. NEVER pay more than 50% upfront. NEVER pay in full before the job is done and you've inspected it.
Question #9: "Will you pull the permits?"
In most areas, roof replacements require permits. The CONTRACTOR should pull them—not you. If they say "we don't need permits" or "you can save money by skipping it," run. That's a huge red flag and can void your homeowner's insurance.
Question #10: "Can I see the materials before installation?"
Good contractors will show you the shingle bundles, underlayment, and other materials on-site before they go up. This prevents bait-and-switch where they quoted premium materials but installed builder-grade junk.
Contractor Red Flags Comparison
| Red Flag | What It Really Means | Risk Level |
|---|---|---|
| Cash-only, no contract | No paper trail, no accountability | 🔴 High |
| Way below other estimates | Cutting corners or bait-and-switch | 🔴 High |
| Door-to-door after storms | Often "storm chasers" who disappear | 🔴 High |
| Pressuring for immediate decision | Doesn't want you comparing prices | 🟠 Medium-High |
| No physical address | Hard to find if problems arise | 🟠 Medium-High |
| Won't provide references | Unhappy customers or no track record | 🟠 Medium |
| No written estimate | Can change price mid-project | 🟠 Medium |
Average Contractor Pricing by Region (2025)
| Region | Average Labor Cost/Sq Ft | Typical Project Range |
|---|---|---|
| Northeast (NY, MA, PA) | $3.50 - $5.50 | $12,000 - $25,000 |
| Southeast (FL, GA, NC) | $2.75 - $4.25 | $9,000 - $18,000 |
| Midwest (OH, IL, MI) | $2.50 - $4.00 | $8,500 - $16,000 |
| Southwest (TX, AZ, NM) | $2.50 - $4.00 | $8,000 - $15,000 |
| West Coast (CA, WA, OR) | $4.00 - $6.50 | $14,000 - $30,000 |
| Mountain (CO, UT, MT) | $3.00 - $5.00 | $10,000 - $20,000 |
My Personal Recommendation Process
Here's exactly what I tell friends and family when they ask how to hire a roofer:
- Get 3-4 estimates. Not 1, not 10. You need enough to compare but not so many you're overwhelmed.
- Throw out the highest and lowest. The sweet spot is usually in the middle. Extremes are often overpriced or cutting corners.
- Check Google Reviews AND BBB. Look for patterns in complaints, not just star ratings.
- Trust your gut. If something feels off during the estimate, imagine how the job will go.
- Get everything in writing. Timeline, materials, price, warranty. No handshake deals.
What Good Contractors Do Differently
The best roofers I know share these traits:
- They show up on time for the estimate (or call if they're running late)
- They explain options without pushing the most expensive one
- They point out issues you didn't know about—and explain why they matter
- They have organized crews with matching shirts or company vehicles
- They clean up every day, not just at the end
- They do a final walkthrough WITH you before asking for final payment
The Bottom Line
Your roof is one of the biggest investments in your home. Spending an extra hour vetting contractors can save you thousands and years of headaches. Ask the hard questions. Demand written answers. And if a deal seems too good to be true, it always is.
I've been on countless roofs and seen the aftermath of both excellent work and catastrophic failures. The difference almost always comes down to who you hire. Choose wisely.
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