What Southern Maine Homeowners Should Know About Insurance, References, Estimates, and Contracts

Paul Landry • November 4, 2026

What You need to know before you hire a contractor

Two white historic houses with chimneys in daylight, set behind shrubs under a clear blue sky

Hiring a contractor is one of the biggest decisions in any home project, and most homeowners make it with very little to go on: a few online reviews, a couple of quotes, and a gut feeling. That's understandable, because most people only do a roof, a new set of windows, or an addition once or twice. But the contractor you choose will affect your project's cost, timeline, and quality far more than the materials you pick.

At M & Son Construction, we've been working with homeowners across Portland, South Portland, Scarborough, Falmouth, Westbrook, Gorham, and the surrounding communities for 12 years, with roughly 20 years of combined industry experience behind our crew. The homeowners who have the best experience are almost always the ones who asked good questions up front, whether they ended up hiring us or not. Here are the ones worth asking, and what a good answer sounds like.


Start With the Basics: Who Are You Actually Hiring?

Before you get into scope or price, confirm the fundamentals.

  • How long has the company been in business, and what is its legal name? A track record in your area matters. It means they've handled Maine's weather, local permitting, and supplier relationships across many projects.
  • Do they have a real business address and a consistent point of contact? You want to know who will answer the phone in month two of your project, not just month zero.
  • Who will actually be on site? Ask whether the company's own crew will do the work or subcontract it, and who supervises it day to day. Both models can work well, but you should know which one you're getting.


Insurance: The Question That Protects You Most

Insurance is the least exciting part of hiring a contractor and potentially the most expensive one to skip. Ask for proof, not just a yes.

  • General liability insurance covers damage to your property caused by the work, such as a dropped tool through a skylight or water damage from an open roof during a storm.
  • Workers' compensation insurance covers injuries to the people working on your home. Without it, a worker injured on your property can create real exposure for you as the homeowner.

Ask for a certificate of insurance and, if you want to be thorough, have the insurer send it directly to you rather than handing over a photocopy. A reputable contractor will do this without hesitation. Hesitation, or an answer like "we'll get that to you later," is a signal worth noticing.


References and Past Work

A contractor who does good work should be easy to verify.

  • Ask for recent references, not just the best ones. Projects from the last year or two tell you how the company works now.
  • Ask for similar projects. A company that's excellent at decks may not be your best choice for structural framing, and vice versa.
  • Look at finished work in person if you can. Photos help, but a completed roof, deck, or addition you can actually see tells you more about workmanship.
  • Read reviews for patterns, not perfection. No company is flawless. What matters is how problems were handled, and whether the same complaint, such as missed callbacks or surprise charges, shows up repeatedly.

The Written Estimate: What It Should Include

A good estimate is specific. Vague estimates are where disagreements start later. Look for:

  1. A clear scope of work describing exactly what will be done, including tear-off, disposal, cleanup, and repairs to anything hidden (such as rotted decking or sheathing).
  2. Named materials, meaning the brand, product line, and color, not just "architectural shingles" or "vinyl siding."
  3. A price breakdown or clear total, along with how unforeseen conditions will be handled and priced.
  4. Permit responsibility, spelling out who pulls permits and who pays for them.
  5. Start date and estimated duration, with an honest note about weather dependence.
  6. Cleanup and site protection, such as how landscaping, driveways, and neighboring areas will be protected.

If any of these are missing, ask. The answers should be in writing.


Contracts, Payment, and Change Orders

Never start a project of any size on a handshake. A written contract should cover the scope, price, schedule, and payment terms.

  • Payment schedule: Be cautious of requests for a large upfront payment. Payments tied to project milestones are a common and reasonable structure. Ask what the deposit covers.
  • Change orders: Projects sometimes uncover surprises, like rot behind old siding. Ask how changes are documented and approved in writing before extra work begins, so there are no surprises on the final bill.
  • Lien and payment protection: Ask how the contractor handles payments to suppliers and subcontractors, so that your home isn't affected by an unpaid bill you didn't know about.

Requirements around contracts and consumer protections can vary, so it's worth checking current Maine and local rules, or asking your contractor to walk you through what applies to your project.


Warranty: Material vs. Workmanship

These are two different things, and both should be in writing.

  • Manufacturer warranty covers the product itself, such as shingles, windows, or siding, and is usually backed by the manufacturer.
  • Workmanship warranty covers the installation and is backed by the contractor. This warranty tells you how much a company stands behind its own work.

Ask how long each lasts, what's covered, what voids it, and how to make a claim. A contractor who answers clearly and has been around long enough to honor past warranties is worth a lot.


Timeline and Communication

A realistic schedule beats an optimistic one. Ask about:

  • When the project could start, and what could delay it (weather, material lead times, permits)
  • How long the work itself should take
  • How you'll be updated, and who your day-to-day contact is
  • What happens if the schedule slips

For exterior work in Southern Maine, weather is a legitimate factor, and a contractor who explains that honestly is more trustworthy than one who promises exact dates regardless of conditions.


Red Flags Worth Noticing

  • Pressure to sign immediately or "today only" pricing
  • A price far below every other quote, with no explanation
  • Reluctance to provide proof of insurance or references
  • No written contract or a vague scope
  • Requests for large cash payments up front
  • Door-to-door solicitation after a storm with no local track record

One of these doesn't always mean a bad contractor, but several together are a reason to slow down.


Getting Started

The best next step is simple: get two or three written estimates, ask each contractor the questions above, and compare the answers as carefully as the prices. If you'd like to see how we handle it, we're happy to walk your property, explain what we'd do and why, and put it all in writing, with no pressure to decide on the spot.


Frequently Asked Questions

How many estimates should I get before hiring a contractor? Two or three written estimates is a reasonable range for most projects. It gives you a sense of the market and a basis for comparing scope, materials, and communication, without turning the process into a months-long chore.

What insurance should a contractor have? At minimum, general liability insurance and workers' compensation insurance. Ask for a certificate of insurance to confirm coverage is current, and consider having it sent directly from the insurer.

Should I pay a deposit up front? Many contractors ask for a deposit to cover materials and scheduling, which is common. The contract should spell out the amount and what it covers, and later payments should be tied to progress rather than due all at once.

What's the difference between a manufacturer warranty and a workmanship warranty? A manufacturer warranty covers the product itself, while a workmanship warranty covers the installation and comes from the contractor. You want both, in writing, with clear terms.

What should I do if the lowest bid is much cheaper than the others? Compare scopes line by line. A big gap often means something is missing, such as lower-grade materials, no tear-off, no permit, less insurance, or no cleanup. Ask the low bidder to explain what's included and why it costs less.

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