Hire a South Shore roofer: 5 questions to ask first

Getting a roof quote takes an afternoon. Reading the quote with the right context takes fifteen minutes, and that fifteen minutes is where most of the risk lives. Five questions, asked in writing, will tell you more about a roofing contractor than any before-and-after photo.

1. What is your Massachusetts HIC registration number?

Every residential roofing contractor working on a 1-to-4 unit owner-occupied home in Massachusetts has to be registered as a Home Improvement Contractor. The registration number must appear on the contract when the project exceeds $1,000. A contractor who hesitates on this question is telling you something.

Verify it yourself at the Massachusetts HIC registration lookup. Takes 30 seconds.

2. Who is the crew on my roof, and are they employees?

There is a meaningful difference between a contractor with a W-2 crew and one who subcontracts to day laborers. Both can do good work. Both carry different risk profiles for you as a homeowner, especially on workers’ compensation.

Ask for a current workers’ compensation certificate of insurance. If the contractor uses subcontractors, ask whether the sub carries their own coverage. If there is no coverage on anyone setting foot on your roof, an on-site injury becomes your problem.

3. Which underlayment and flashing are you using, by product name?

The shingle is the visible part of the roof. The underlayment and flashing are the parts that determine whether the roof leaks in a nor’easter three years from now. Premium shingles over builder-grade felt paper is not a premium roof.

Ask for product names. Ice-and-water shield at eaves and valleys should be specified. For coastal towns like Scituate, Hull, Marshfield, and Duxbury, ask about wind-rated nailing patterns (six nails per shingle rather than four is a common upgrade for high-wind zones) and stainless-steel flashing where salt exposure is a concern.

4. What happens to my existing decking?

Older South Shore homes, especially in Plymouth, Kingston, Middleborough, and Halifax, commonly have plank decking that dates to the original build. When old shingles come off, some planks are rotten. The question is not whether there will be decking replacement; the question is how it is priced.

Ask whether decking replacement is time-and-materials, and at what rate. Ask for the rate per sheet of plywood and the rate per linear foot of plank. Ask how that rate is documented on the final invoice. “We’ll let you know” is not an answer.

5. What does the final payment schedule look like, and when do you sign off with the town?

Massachusetts requires a written contract for home improvement work over $1,000. The contract should state a payment schedule. A reasonable schedule for a roofing job is something like:

• A deposit at signing (no more than a third in most situations).
• A progress payment when the job is underway.
• A final payment after the town has signed off on the permit close-out, the site is cleaned, and the final invoice is delivered.

If a contractor asks for full payment upfront, or for the full balance the day the last shingle goes on, something is off. If the town never sees the permit closed out, you have a roof but you do not have documentation of an inspection, and that matters when you sell the house.

One bonus question

“Can I email these five questions to you and get the answers in writing?” A good contractor will say yes without hesitation. That email becomes part of your file, and if anything goes sideways later, you have a dated record of what was promised.