How to Choose Roofing Contractor: Complete Guide and FAQ

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A reliable, durable, long-lasting roof is one of the most profitable and successful investments. However, when it comes to installing a new roof or repairing or renovating an old roof, you need the expertise of a professional Roofing Contractor. It demands professional training and skills, specialized equipment and tools, carefully selected materials, and knowledge of complete details of architectural craftsmanship. You need a team of not just average builders but also experienced roofers, preferably from among local contractors.

Dennis Tchernov - Roofing contractor
Dennis Tchernov – Roofing contractor

Let’s Consult a Specialist

This article will guide you on how to differentiate between reputable and unscrupulous contractors, offer financing, how to study offers, and finally, how to choose roofing experts based on specialization. It will also explain why local companies are often a better choice and provide a few top questions you should ask when you first meet with a local roofing company representative.

For help and information, we turned to an expert in the field, Dennis Tchernov, the head contractor at ID Flat Roof, which has provided roofing and other construction services in Boston and Massachusetts for over 20 years.

Choosing Between Good and Unscrupulous Roofing Contractors

Dennis Tchernov

«Having worked in the Boston construction market for many years, I can say that a good roofing contractor has certain key indicators distinguishing conscientious professionals from those lacking experience or willingness to work well. So, how do you hire the best roofing contractor in your city?»
Denis Tchernov ID Flat Roof - General Contractor


The first thing to check is not the portfolio or the contractor’s reviews (on the company’s official website, independent sites, social networks, or local newspapers). Reputable contractors committed to safety work always pay special attention to licensing and insurance of their activities, even if it is a small roof repair. This means that the company not only has the license, insurance, proper certificate, and permissions to work in their field but also adheres to industry standards. Needless to say, when it comes to installing new roofs in private and commercial buildings, safety and property protection are very important.

contgract with roofing contractor

Pricing Policy

The second significant indicator is a clear, transparent, and reasonable pricing policy. A trustworthy contractor is interested in ensuring that its clients understand what they are paying money for, what work the contractor will do, and what responsibilities both parties bear. Why is this important? Suppose a contractor does not provide a detailed and written estimate, or refuses to include it in the contract. In that case, there’s a chance you might encounter hidden charges and imposed services in the final bill that you were unaware of beforehand. ID Flat Roof always provides its clients with detailed and written estimates and, what is more, offers financing options that take into account the wishes and budgets of clients.


The third indicator of a roofing contractor with high-quality customer service is reputation, which must be supported by real reviews and a portfolio. We always recommend turning to local contractors, as it benefits both customers and local contractors. Local roofing companies should have a list of references and positive reviews online. Check platforms like Yelp, Google Reviews, and the Better Business Bureau to get up-to-date information on the company’s performance in recent years.

Brookline, Massachusetts PVC roof
Brookline, Massachusetts PVC Roof
Lawrence, Massachusetts PVC Roof
Lawrence, Massachusetts PVC Roof
PVC Roof Installation, Waltham
PVC Roof Installation, Waltham


You can also find reviews of our completed projects in Massachusetts and photos of installed, restored, and repaired roofs on our official website. If you want to hire a reliable contractor in Boston or nearby cities, you can personally visit our office and check completed ID Flat Roof residential and business roof projects.

Manufacturer Partner

Finally, good and professional roofing contractors, dedicated to their work, collaborate with material suppliers directly. This is beneficial both for clients and roofers. They get access to a wide range of options—not just time-tested materials but also modern membranes with the best protection like TPO, and PVC, as well as roofs with solar panels, or roofs with decks—at reduced prices due to direct business partnerships between independent roofing contractors and manufacturer.

Choosing a Roofing Contractor Based on Specialization

Roofing Constractor - ID Flat Roof - Dennis Tchernov

There are several categories of roofing contractors. For example, our company specializes in flat commercial and residential roofs, as well as modern, energy and cost-efficient roofing materials with a lifespan of over 20 years. To add, we work not only with residential property but also with business and commercial property.

PVC Roofing: Benefits and Advantages

Roof Type

Nevertheless, roofing is a diverse field, and contractors may specialize in different types of roofing systems and materials. Pay attention to the type of roof you have or want—it could be flat, sloped, gabled, or even domed. Residential roofs differ from commercial roofs in terms of design and materials. Make sure the contractor has experience with your specific type of roof. If the company is local, request photos of completed projects in your area.

Roofing Materials

Contractors often specialize in particular roofing materials such as PVC, asphalt shingles, metal roofing, tile, or slate. Each material has its installation methods, sealing, and maintenance requirements, so choose a contractor with expertise in the material you prefer. As mentioned earlier, our company specializes in modern materials, but we also work with time-tested solutions that have been used in the state for the last 50 years—from BUR (built-up roof) and EPDM roofs to asphalt roofs.

Additional Tasks

Some contractors offer additional services like gutter installation, skylight repairs, or insulation inspection. If your project involves these elements, a contractor who can handle multiple aspects may be beneficial. Our company performs the entire range of additional work—from installing skylights and chimneys to mounting drainage systems and gutters.

🟩 Benefits of Hiring Local and Independent Roofing Contractors

If you live in Boston or another city in Massachusetts, we are happy to offer our services. Opting for a local roofing company has several advantages:

  • ✅ Our company comprises licensed contractors who are well-versed in MA building codes and regulations, ensuring compliance and avoiding potential legal issues. We know all the bureaucratic pitfalls and strictly follow all rules and regulations. Moreover, we know the specifics of the Boston homeowner’s insurance coverage, insured events, and payments for homeowners.
  • ✅ We rely on our community’s reputation like independent contractors or other conscientious local companies. Surely, you have friends or colleagues who have already applied for roofing services. In addition, you can meet with our expert roofer to tell us more about your projects or check reviews on our website.
  • ✅ The right roofer and good contractor always maintain feedback with clients. If problems arise after the project is completed, local contractors are easier to contact and can quickly address any workmanship and business issues. We provide both workmanship warranty coverage and warranty on brand materials.

Warning Signs to Avoid with a Roofing Contractor

❌ No Licenses and General Liability Insurance

If a contractor cannot provide proper license and insurance, it’s a major red flag. At ID Flat Roof is a licensed contractor, and we believe that any professional activity should be regulated by supervisory authorities and insured with protection against unforeseen circumstances. We strongly recommend cooperating with licensed contractors only.

❌ Pressure on the Client

Another red flag is high-pressure sales tactics. If you are rushed into signing a contract, not given time to carefully and leisurely study and compare offers from different companies in your city, it is a sign that you are dealing with a company not committed to long-term cooperation.

❌ Verbal Agreements Only

Avoid verbal agreements with any roofer at all costs. Always insist on a written contract with complete details to protect your interests. This way, you can defend your rights in court if disputes arise with the contractor. At our company, we always insist that all duties, responsibilities, deadlines, warranties, references, and estimates are documented in the contract before starting work regardless of the project scope and budget. Pay attention to writing any conditions and warranties that are important to you in the contract. It becomes a guarantee of the client’s safety and peace of mind.

List of Questions to Ask from the Very Beginning

Over the years, we have identified the key questions you should ask before hiring any contractor or building team, especially a roofing contractor. This is important for both us as professional contractors, and you as a client. Before hiring a roofing contractor, ensure you ask the following questions:

  • Where can I look up your current license and professional insurance information? The contractor is responsible for providing you with all required information.
  • Can you provide references and where I can read real reviews? If you contact a local roofer, ask the consultant to show you photos of completed projects that you might have seen on the streets of your city.
  • How long does it take to install or repair a roof? Can you carry out urgent repairs or roof inspections? Although project timelines vary depending on individual factors, the roofing company can immediately provide an estimated timeline.
  • What is the payment schedule? The contract should indicate a detailed written estimate and the procedure for making each payment, the schedule, and the dates when you must make payments. Another critical point is unforeseen payments that may arise during the work process due to additional stages or changes in the cost of materials.
  • Do you offer warranties? It is advisable to contact roofers who work directly with material manufacturers and know how to work with them to receive a maximum or lifetime warranty from the manufacturers.
  • How do you handle unexpected workmanship issues? Although roofing projects usually proceed according to a standard plan, unforeseen force majeure events sometimes occur. Clarify how the contractor will act in this case and how to agree on new conditions with the client. That is why any client or contractor commitment should be discussed in advance and included in the contract.
  • Who will be on-site? It is advisable to work with contractors who have complete roofing crews and will not rely on subcontractor roofers. However, if the contract covers such work, the contractor can expect to invite highly specialized specialists (for example, experts from the materials manufacturer).

Conclusion: Compare Offers and Choose a Local Contactor

Choosing the respectable and right roofing contractor in your city requires diligence and careful consideration. By distinguishing between reputable and unscrupulous companies, selecting based on specialization, preferring local contractors, and asking the right questions, you the homeowner can ensure that your installation, renovation, or replacement roofing project is completed successfully and to your satisfaction.

If you want to learn more about roofing services in Boston, MA, you can contact our specialists at ID Flat Roof, ask your questions, visit our office, or request an estimate online.

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Denis Tchernov
Main Contractor at ID Flat Roof

Denis is the driving force behind ID Flat Roof, a leading company in Boston specializing in flat roof repair and installation for over 20 years.
Denis excels in PVC, TPO, EPDM, and rubber roofing. His meticulous approach ensures quality and customer satisfaction.
Denis incorporates cutting-edge solutions like skylights and solar PV roofing.