Frequently asked questions

Plain answers about how Hamilton Management works on Chebeague Island. If yours isn't here, schedule a call with John.

What does Hamilton Management do?

Two things, on Great Chebeague Island, Maine. We run renovation and repair projects, scoping them, pricing them as one number, and building them with a robust network of island contractors. And we manage houses as rentals for owners who aren't in them enough, with an island team handling readiness, guests, cleaning and provisioning. Seasonal close-down and open-up of camps and cottages sit alongside both. We're the first dedicated property management company on the island, and we're run by a ninth-generation islander.

Where do you work?

All of Great Chebeague Island. We don't serve other Casco Bay islands or the mainland. If your house is on Chebeague, it's in our territory, wherever it is on the island.

How do I get started?

Schedule a peace-of-mind call with John at https://calendly.com/johnemery/peace-of-mind-call or email john@hamiltonmgt.com. Tell us about the house and what's been on your mind, and we'll tell you what we'd do first and whether we're the right fit. There's no pitch and no obligation. If a project or a rental makes sense, the next step is a walkthrough.

Do I need to be on the island to work with you?

No. Most of our clients are away for most of the year. Walkthroughs, projects, rentals and seasonal services all run without you present. You approve scope and spending; we handle the rest and keep you informed with photos and plain-language updates.

What kinds of projects do you manage?

Deferred maintenance and the improvements you've been meaning to make. Roofs, sills, shingles and trim. Decks, porches and screen porches. Kitchens and bathrooms. Floor refinishing and painting. Windows and exterior doors. Garage and outbuilding conversions to living space. Automatic standby generators. Septic evaluations and replacements. Chimneys, heating and insulation. Whole-house refreshes before a sale or a rental season.

How does a project run?

We walk the house and write a scope of what's actually there. You get one price for the work, our fee stated alongside it, and a schedule that's honest about the barge and permitting. Nothing starts until you approve it. Island contractors get first call; mainland specialists come in when the island doesn't have the trade. We source materials, schedule the barge and stage on-island. We're on site through the job and send progress photos. Change orders come to you in writing before anyone proceeds.

How is the project management fee calculated?

It's quoted with each job, in writing, before anything starts, and shown as its own line next to the cost of the work — never buried in a tradesperson's invoice. Architectural and engineering fees, permits, freight and materials are shown as their own lines too. Ask on the first call and we'll walk you through how a project like yours is typically priced.

Who actually does the work?

Independent island contractors first — a robust network that includes Mark Heels, Jason Hamilton, Doug Ross and Rich Plumbing, with MODGRP Architecture for design — backed by mainland specialists when the island doesn't have the trade. Each contracts directly with you and carries their own insurance. Hamilton Management scopes, schedules, coordinates, checks the work and handles logistics; we don't perform the trade work, we don't do plumbing, and we don't do dock or float work.

Can I use tradespeople I already know?

Yes. We coordinate the vendors an owner already uses rather than replacing them. If you have a carpenter or electrician you trust, tell us and we'll build the schedule around them.

How do payments work on a project?

Your choice, stated in the agreement. You can pay each tradesperson directly on their own invoice. Or, at your election, Hamilton acts as disbursing agent: you write one consolidated check, we pay the trades, and you receive one statement with a full accounting.

How long does a project take on an island?

Longer than the same project in Yarmouth, and we'll tell you the real number. Vehicles and oversized freight reach Chebeague by barge, and the barge doesn't run all year, so materials are ordered ahead of the seasonal cutoff. Town permitting and septic approvals run on the town's calendar. We plan backwards from those constraints and give you the honest date rather than the hopeful one. A project scoped in the fall can often be built over the winter and ready by summer.

Do you work with architects and engineers?

Yes. Where a project needs an architect, an engineer or a septic designer, we bring them in early and their fees show as their own line so you can see exactly where the money goes.

What does rental management include?

Setup covers readiness work, repairs and a deep clean by island contractors, staging, photography, positioning and listing. Ongoing management covers marketing, bookings, guest screening and communication, turnover between guests, grocery stocking from Doughty's Island Market, and checks on the house between bookings, with every booking reported to you in both directions.

What does rental management cost?

A one-time setup fee by property size, then a share of rental revenue on a twelve-month term, both stated in your agreement before you sign. Turnover and cleaning are quoted separately by property size and billed to the guest as part of the stay. Ask on the first call and we'll show you how the numbers typically work for a house like yours.

Do I need a real estate license, or do you?

Neither. Maine does not require a real estate license for rental or property management, so Hamilton manages rentals directly for owners.

How does the money flow on a rental?

Guest payments are made to Hamilton and held in a segregated client account, then disbursed to you monthly, less fees, with a statement showing every booking, every fee and every tax dollar. You remain the contracting party with each guest.

Who handles Maine's lodging tax?

We do. Maine's 9% state lodging tax is charged to the guest on top of the rent. Hamilton registers with Maine Revenue Services, collects the tax on every booking it handles, holds it in a dedicated account, and remits it. You don't touch it. Cleaning and turnover charged to a guest are inside the taxable amount even though they sit outside our management fee.

What if a booking comes through Airbnb or Vrbo?

Those platforms collect and remit the lodging tax themselves. Hamilton reports that booking as exempt rather than taxing it a second time. Nothing is ever taxed twice.

What stays my responsibility as the owner?

The Town of Chebeague Island short-term rental ordinance, Maine landlord-tenant law, short-term-rental liability coverage on your insurance, income tax on rental proceeds, and any booking you take independently of Hamilton. We'll tell you plainly what each one requires before you sign.

Can I keep the weeks I want for myself?

Yes. The calendar is yours. Many owners keep their own summer weeks and rent the rest; we fill the weeks you release.

Can you manage my rental through the winter?

Yes, with one condition. A house that keeps its water on year-round must have a permanently installed automatic standby generator with an automatic transfer switch. If yours doesn't, we quote the install as a project, or the house drains for the season.

What is Put Her to Bed?

Seasonal close-down, a flat-fee hands-on service handled with our island network. Water shut off and lines blown out, water heater drained, well pump protected, traps and toilets antifreezed, heat set or systems drained, propane topped, furniture and grills stored, storm windows in, gutters cleared, and a full photo walkthrough sent the same day. $650 to $1,200 depending on how many systems the house has.

What is Wake the House?

Seasonal open-up, the mirror of Put Her to Bed. Water on and the system watched for leaks, every fixture and appliance started and tested, a full winter damage inspection of roof, sill, siding, ceilings and foundation, screens in, furniture out, deep clean coordinated. The photo set arrives the day before you do. $650 to $1,200 by systems.

When should I book seasonal services?

Book Put Her to Bed before the first hard freeze and Wake the House at least two weeks before you arrive. The fall schedule fills fastest; get on it early.

Why do unoccupied houses in coastal Maine need watching?

Because a supply line that lets go in January can run for weeks before anyone knows, a heating system that quits in a cold snap freezes pipes within a day, and a house with no eyes on it through a nor'easter is a house at risk. Insurers know this. So does anyone who's opened a summer house in May and found what winter did.

How do materials and freight get to Chebeague?

By barge, which runs seasonally and constrains construction logistics all year. We source materials, make the mainland yard runs, schedule the barge, meet the landing and stage on-island, for owners and for the contractors working on Chebeague. Big orders are timed to beat the seasonal cutoff so winter work isn't waiting on a truck that can't come.

Why do island tradespeople get first call?

Because the people who fix your house should be people who'll see you at the store, on the boat and at town meeting for the rest of their lives. Our network — Mark Heels, Jason Hamilton, Doug Ross, Rich Plumbing and others — has been working on these houses for years. Work gets done right on Chebeague because it has to, and keeping trades on the island keeps the island a year-round town.

Who runs Hamilton Management?

John Emery, a ninth-generation Chebeague islander descended from Ambrose Hamilton, who settled the island in the 1750s. John grew up working on lobster boats with family here, is on Chebeague several days a week year-round, and is moving back to the island full time in the near future.

Why does Hamilton Management exist?

To fight atrophy: houses deteriorating unoccupied, tradespeople leaving for the mainland, and money arriving with the July ferry and leaving the same week. Chebeague's year-round community is under the same seasonal-conversion pressure that has already reshaped Deer Isle, Stonington, Vinalhaven, Nantucket and Martha's Vineyard. Our answer is to make it easy to spend money on the island, with island people, on work that keeps houses alive and trades at home.

What is the Scoreboard?

Three numbers we publish every year so our claims can be checked rather than taken on faith: island jobs created, dollars paid to Chebeague Island trades, and year-round housing units held and occupied. The first Scoreboard publishes at the close of our first full year.

Is Hamilton Management insured?

Hamilton Management carries its own business insurance, and every tradesperson we bring to your house carries their own. Ask us for current certificates before work begins.

How do I reach you?

Schedule a peace-of-mind call with John at https://calendly.com/johnemery/peace-of-mind-call.