Your roof is one of the most important—and expensive—components of your home. When it’s time for a repair or replacement, choosing the right roofing contractor is a decision that will impact your home’s safety, value, and your peace of mind for decades to come. But in a sea of options, how do you separate the true professionals from the storm chasers and fly-by-night operators?
As a family-owned business that has served the Delmar community since 1988, we’ve seen it all. We believe an educated homeowner is the best customer. That’s why we’ve compiled this essential list of 12 questions you must ask any roofing contractor before you sign a contract. Arm yourself with this checklist to ensure you hire a qualified, trustworthy, and reliable professional for your Delmar home.
The Non-Negotiables: Before You Even Get an Estimate
These first three questions are so critical that if the answer to any of them is “no,” you should walk away immediately.
1. Are you licensed and insured in Delaware and Maryland?
This is the single most important question. A reputable contractor will have both a state license and comprehensive insurance.
– Licensing: In our area, a contractor should have licenses for both Maryland (MHIC) and Delaware. For example, our licenses are MHIC 127989 and DE LIC 2009107105. This proves they have met the state’s requirements for knowledge and experience.
– Insurance: They must carry two types of insurance: liability insurance (to protect your property from damage) and worker’s compensation insurance (to protect you from being sued if one of their employees is injured on your property). Ask to see the insurance certificates. A legitimate contractor will be happy to provide them.
2. Will you provide a detailed, written estimate?
A verbal quote or a price scribbled on a napkin is a major red flag. A professional estimate should be a detailed document that includes:
– A full description of the work to be done (e.g., tear-off of old roof, installation of new shingles).
– The specific materials to be used (e.g., GAF Timberline HDZ shingles, color: Charcoal).
– The total cost, including a breakdown of materials and labor.
– The payment schedule.
– The estimated start and completion dates.
3. Can you provide a list of local references?
Past performance is the best indicator of future results. A contractor with a long history of happy customers in the Delmar area should be eager to share references. Ask for the names and numbers of at least 3-5 recent customers, and then actually call them. Ask about their experience with the contractor’s communication, timeliness, and quality of work.
Digging Deeper: Questions to Assess Expertise and Professionalism
Once a contractor has passed the initial screening, these questions will help you gauge their expertise and business practices.
4. How long have you been in business in the Delmar area?
Look for a contractor with a long, stable history in your local community. A company that has been around for 10, 20, or 30+ years (like us!) has a proven track record and a reputation to uphold. Be wary of “storm chasers” who show up after a big storm and disappear just as quickly.
5. Are you a certified installer for any roofing manufacturers?
Top roofing manufacturers like GAF and Owens Corning offer certification programs to contractors who have been factory-trained in their installation methods. This is a mark of quality and professionalism. For example, being a GAF Certified™ contractor often allows a roofer to offer enhanced warranties that other contractors can’t.
6. Who will be performing the work? Are they employees or subcontractors?
It’s important to know who will be on your property. While some contractors use trusted subcontractors, a company that uses its own trained and vetted employees often has better quality control.
7. What is your warranty on workmanship?
There are two types of roofing warranties: the manufacturer’s warranty (which covers defects in the roofing material itself) and the contractor’s workmanship warranty (which covers errors in the installation). A confident, quality-focused contractor will offer a solid workmanship warranty of at least 5-10 years. Get the details in writing.
8. “How will you protect my property during the project?
A roofing project can be messy. Ask the contractor what steps they take to protect your landscaping, siding, and driveway from damage. This includes using tarps to cover plants and walls, and a plan for cleaning up nails and debris at the end of each day.
9. What is the plan for unexpected issues, like rotted decking?
It’s not uncommon to find soft or rotted wood decking after the old shingles are torn off. A professional contractor will have a plan for this. Ask how they handle such discoveries and what the cost will be for replacing damaged sections of decking (e.g., a per-sheet price).
10. What is the payment schedule?
Be very wary of any contractor who asks for the full payment upfront. A typical payment schedule might be one-third to start the project, one-third at the halfway point, and the final one-third upon completion and your satisfaction. Never pay in cash.
11. How long will the project take, and what happens if there’s a weather delay?
A contractor should be able to give you a realistic timeline for your project (e.g., 3-5 days for a typical roof replacement). They should also have a clear policy for how they handle rain or other weather delays to ensure your home remains protected.
12. Who is my main point of contact for this project?
Clear communication is key to a stress-free project. You should have a dedicated project manager or point of contact who you can call with any questions or concerns that arise during the installation.
The Smarter Choice for Your Delmar Roof
At Smarter Improvements, we’re proud to be the roofing contractor Delmar homeowners have trusted for over three decades. We are fully licensed and insured, GAF Certified, and we stand behind our work with a rock-solid workmanship warranty. We invite you to ask us these questions and more.
Ready to work with a contractor who puts quality and integrity first? Contact us today for a free, no-pressure consultation and estimate.
Frequently Asked Questions (FAQ)
What are the red flags to watch out for when hiring a roofer?
Major red flags include: asking for full payment upfront, not having a local address or phone number, pressuring you to sign a contract immediately, offering a price that is “too good to be true,” and not being able to provide proof of licensing and insurance.
Is the lowest bid always the best choice?
Almost never. An unusually low bid is often a sign that the contractor is cutting corners, either by using substandard materials, hiring unskilled labor, or not carrying proper insurance. When it comes to your roof, it’s always better to pay a fair price for quality work from a reputable company.
Do I need to get a permit for a roof replacement in Delmar?
Yes, a permit is typically required for a full roof replacement in Delmar and the surrounding areas of Sussex County, DE, and Wicomico County, MD. A professional roofing contractor will handle the entire permitting process for you as part of their service.






