7 Questions to Ask a Middletown, DE Roofer

1. is the roofer registered with the state, and does the town know them?

Delaware law requires a business that does construction services to register with the Delaware Department of Labor's Office of Contractor Registration before work begins in the state, on top of its Division of Revenue business license. The state publishes a registry of the businesses it has certified, and you can search it by name or certificate number. Ours is Delaware Contractor Registration No. DE-2026-000015163, held by Home Fortress Construction LLC under the trade name Home Fortress Roofing & Construction. The registry showed it valid until 06/03/2027 when we looked on October 30, 2026.

The Town of Middletown asks for something separate. Its Business Licenses page says the Town requires all contractors working within town limits to get a business license. Its FAQ takes up the question of whether a State or County license is enough and answers that all contractors and subcontractors must have a valid Town of Middletown business license to work within Town limits. Ask to see the state registration and the Town license, and ask whether subcontractors will be on your roof.

2. what insurance covers the crew and your house?

A roof job puts people on a steep slope above your home, so ask for a certificate of insurance that shows general liability coverage and workers' compensation. Have the roofer's insurance agent send it to you directly, so you are reading the current policy.

The state's registration checklist asks applicants for workers' compensation coverage for Delaware. That was true on the day they applied, so ask for a certificate that shows coverage now. Ask every roofer on your list, us included.

3. who applies for the town building permit, and whose name is on it?

The Town's Permits, Licensing and Inspections page lists replacing or repairing roofing among the work that needs a building permit. It says the permit confirms the work meets the International Building Code and the Code of the Town of Middletown, and that each phase of the work is inspected by the town code official. When the work is done, an inspection is scheduled with the code officials so the permit can be completed.

The Town's FAQ says an application should include the contractor's details, and that an incomplete application delays the process. It also says a permit is valid for one year after approval, and that when a contractor is changed, the original permit holder stays legally responsible until they vacate the permit and the new contractor is formally added. So ask who applies, whose name goes on the permit and who calls for the inspection. The Town's permits line is (302) 378-1171. Its pages speak of work inside Town limits, so confirm your address is inside them before you rely on this list.

If an insurance claim is paying for the roof, the scope of loss is one more document to read before work starts. Our Delaware roof insurance claim guide walks through it.

4. what does the written estimate say?

Delaware's home improvement regulation counts roofs, gutters, downspouts and siding as home improvement. It requires a written contract with all material terms, such as the item or service you are buying and the contract price. The Department of Justice's summary adds that the contractor must fill in the final terms before you are asked to sign, must give you the company's name, address, telephone number and e-mail address, and may not claim that a binding contract is only an estimate. The Department's FAQ says the merchandise has to be described well enough for the buyer to evaluate what is on offer, so a single line reading "roof replacement" is thin.

On a roof, ask that the paper name the shingle line and color, and ask what happens to the price if the deck under the old shingles needs work. On a replacement the old shingles and underlayment come off down to the wood deck, so the deck can be checked before anything new goes on.

Our estimate is free and follows a free inspection. We photograph the roof by drone, show you the pictures and tell you whether a repair will do. One Google reviewer, kristina rice, wrote that we “provided tons of pictures and videos to show the current condition.” Another, Lisa Juhl, wrote that we “did a thorough assessment” and sorted the changes into “must do” and “recommendations.”

5. which materials go on, and who stands behind them?

Ask for the brand, the shingle line and the color in writing. The Middletown replacements we have published went on in Owens Corning Duration, in Williamsburg Gray on a Parkside home and in Evergreen Mist on a second house. On a Magnolia job we used a complete Owens Corning Duration roofing system, with Owens Corning components from start to finish.

A replacement comes with a lifetime manufacturer warranty, so ask us for the written warranty terms for the system you choose. With any roofer, find out which promises made out loud are in the contract. The Department of Justice's summary says a home improvement contractor must put into the contract every affirmation of fact or promise that amounts to an express warranty, and that a contractor who wants to disclaim or limit a warranty must do it clearly and conspicuously, with your initials. A manufacturer's warranty is the shingle maker's promise about the product, so ask separately who answers for the installation, and get that in writing too.

6. when does the work start, and who cleans up?

The Department of Justice's summary says you must be given an approximate completion date unless the contract clearly says none will be given, and that the contractor must finish by the listed date unless events beyond their control cause a delay or you agree in writing to a later one. Put the start window and the finish date on the contract, and ask what happens if rain pushes the schedule.

Then ask about the yard. Who protects the landscaping and the driveway, and how are nails picked up when the crew is done? Our crew cleans up the property before leaving, and we then walk the finished job with you. One Google reviewer, James Stubbs, wrote that “his crew completed the job in one day” and that “His crew spent close to an hour making sure the property was cleaned up after the job was finished.” That is his experience, and your timeline depends on your roof, so get your own in writing.

7. who can vouch for the work?

Read the roofer's Google reviews and see how the company answers a critical one. Then ask for the address of a recent job near you, or a phone number for a homeowner who will talk. Two of our published roof replacements are in Middletown, and the photos from both are on our Google Business Profile.

Last, notice how the first meeting feels. A Google reviewer, Steven Cavagnino, wrote that we “made no huge push for me to sign any contract at the time.” Collect at least two estimates and set the answers above side by side before you sign anything.

Where to start

The inspection is free. We fly a drone over the roof, show you the photos and tell you plainly whether you need a repair or a replacement, and if a small roof repair will do, that is what we quote. Financing is available; ask about it at the inspection, or call (302) 314-1025.

Sources, read October 30, 2026: Town of Middletown, Permits, Licensing & Inspections, Business Licenses and FAQs; Delaware One Stop, Construction Contractors (Department of Labor contractor registration) and the Delaware contractor registry; Delaware Department of Justice, Home Improvement Regulation Summary (revised October 31, 2023) and Home Improvement Regulations FAQ. Job facts: our Google Business Profile posts of July 30 and August 11, 2026.