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9 Questions You Shouldn’t Skip When Hiring a Roofer

The man is working on a roof wearing safety gear.

Choosing the right roofer is more than just hiring a contractor—it’s about investing in the safety and longevity of your home.

In Chicagoland, where harsh winters and unpredictable weather can quickly turn a small roof issue into a big problem, the stakes are even higher.

But here’s the reality: many homeowners make costly mistakes when choosing a roofer. Some skip the critical research, others overlook important questions, and many get lured in by the lowest price, only to pay for it down the line.

In this guide, we’ll break down nine essential factors to help you pick a roofing pro, learn what the red flags are, and why hiring an experienced roofer is a must. You’ll have all the tips you need to make a smart, lasting choice.

Key Takeaways

  • Rather than going for a quick, one-size-fits-all fix, a pro roofing team will tailor solutions to handle the specific weather.
  • The choices you make today can determine how long your roof lasts tomorrow.
  • A trustworthy roofer should provide a warranty, showing they stand by the quality and durability of their work.

Are They Properly Licensed and Insured?

Don’t take shortcuts when hiring a roofer—make sure they’re fully licensed and insured. Choosing an unlicensed contractor might seem like a way to save money, but it’s a gamble that could cost you big in the end. Without a license, there’s no guarantee they have the necessary skills or knowledge to get the job done right.

Always ask for proof of their license and insurance before any work begins. It’s the smart move to ensure you’re protected and that the job is done right—no surprises, no headaches, just peace of mind.

Do They Offer a Clear, Detailed Estimate?

A thorough, transparent estimate is a sign you’re dealing with a true professional who’s clear about both the work and the costs involved. If the roofer can’t provide specific details about materials, labor, or the project timeline, that’s a red flag. 

A reliable estimate should include:

What to Look For Why It’s Important
Materials Clear details on the type, quality, and quantity of materials ensure you’re not overcharged with unexpected costs.
Warranty Coverage  An understanding of the warranty coverage for the proposed material and labor coverage.
Project Communication  An understanding of how you and contractor will communicate through out the project and what checkpoints you’ll be updated on.

What’s Their Warranty Policy?

A roof is a big investment, so you want a roofer who’s confident in their work and willing to back it up with a solid warranty. Without it, you’re taking a gamble that a homeowner should not risk. Look for two types of coverage:

  • Material Warranty: Covers the roofing products, addressing any material defects.
  • Workmanship Warranty: Protects you against installation issues, covering any labor-related problems.

Ask the roofer these key questions:

  • What’s actually covered? Get clarity on what’s included and excluded.
  • How long is the warranty valid? Longer terms show confidence in their work.
  • Are there specific conditions or fine print? Understand any limitations to avoid surprises.

A dependable warranty gives you peace of mind and shows the roofer’s commitment to quality.

Are They Highly Experienced with Your Specific Roof Type?

Think of it like cooking a complex recipe—if the chef isn’t familiar with the ingredients, the outcome could be a disaster. The same goes for your roof.

Different roofing materials, like asphalt, metal, or tile, each come with their own set of challenges and require specialized expertise. If a roofer doesn’t have experience working with your specific material, they might overlook important details or use the wrong techniques—resulting in costly mistakes and potential long-term issues.

Make sure to ask if the roofer has experience with your particular roofing type. Their expertise will ensure the job is done right.

Do They Know How to Handle Chicago’s Weather?

With dramatic temperature swings and unpredictable storms, your roof is always on the front lines, fighting off the harsh elements year-round.

A roofer unfamiliar with these extremes could easily overlook important details that keep your roof protected. You need a roofing expert who understands how to guard against everything from snow buildup and ice dams in winter to intense UV rays and rainstorms in summer.

An experienced roofer in Chicago will know exactly how to install and maintain your roof so it can handle the city’s tough climate. They’ll anticipate potential issues before they become costly problems.

Does Safety Come First?

Protecting your home starts with protecting those who work on it. With all the risks involved, you need a roofing crew that makes safety their top priority. Here’s how to find out:

  • Do they prioritize training?
  • Are they serious about safety gear?
  • Are they OSHA-compliant?

How Do They Handle Surprises Along the Way?

When it comes to roofing, surprises are often part of the deal—whether it’s rotting wood, water damage, or hidden mold. These issues can be frustrating, but how your roofer handles them can make all the difference.

A true professional doesn’t just point out problems and leave you in the dark. They should be proactive, explaining exactly what’s wrong, how it affects your roof, and the best course of action to take.

You want someone who doesn’t just highlight issues but offers real solutions, without adding unnecessary stress.

What Do Local Homeowners Say About Them?

When picking a roofer, reputation matters, as a strong local reputation reveals a lot about a roofer’s quality, dependability, and integrity.

You want more than just glowing online reviews, you want feedback from local homeowners and businesses who’ve experienced their work firsthand. Here’s what to ask local references:

  • Did the roof last through seasons?
  • Was communication smooth?
  • Any hidden fees?
  • Would you rehire?

Do They Take Care of Cleanup?

The job isn’t complete until the cleanup is done right. 

A fresh roof shouldn’t come with a side of chaos. After the job is done, the last thing you want is a yard filled with nails, broken shingles, and debris. Not only does it look bad, but it’s also a safety concern for both your family and pets.

Make sure your roofer takes responsibility for clearing away the mess, so you can enjoy your new roof without the hassle.

Your Roof, Our Priority at M&M Home Remodeling Services

At M&M Home Remodeling Services, we believe in providing long-lasting solutions with top-quality materials, all backed by solid warranties. Whether you’re looking for a new roof or simply need expert advice, we’re here to guide you every step of the way.

No hard sales, just honest, helpful information to help you make the best decision for your home. Call us at (708) 756-7800, and let’s chat about your roofing needs!

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