12 Questions to Ask Before Hiring a Nantucket Caretaker

If you own a house on Nantucket and you don't live there year-round, your caretaker is the single most important vendor in your life. The roofer might charge you more in any given year. The landscaper might be in your house more often. But the caretaker is the person whose visits keep the heat running, the pipes from freezing, the windows secured, and the small problems from becoming the large ones.

Hiring a good one is harder than it should be. The market on Nantucket is tight. The good caretakers are usually full and don't advertise. Word-of-mouth dominates, which means new owners often end up with whoever returned the email. And the work itself is hard to evaluate from afar — the only thing you really see, sitting in your office in Manhattan or Atlanta, is what the caretaker chooses to tell you.

This guide is meant to help. Twelve questions to ask in the initial conversation, what to listen for in the answers, and what to look for in the documentation pattern that gets established once they start working for you.

1. How many properties do you currently caretake?

There's a reasonable range here, and it varies by the model. A solo caretaker doing weekly walkthroughs and direct vendor coordination might handle 15 to 25 properties. A larger firm with a team of caretakers might do 80 or more.

What you're listening for is whether the answer comes with a structure. "I do a couple dozen" is less reassuring than "I currently caretake 22 properties, organized in three weekly route loops, with my partner handling overflow and storm coverage." The second answer means there's a system. The first means there's a guy with a truck.

2. Walk me through your weekly visit. What do you actually do?

The right answer is specific and ordered. They walk a property in a consistent way — exterior first, mechanical room, kitchen, bathrooms, run faucets, flush toilets, check thermostat, walk the bedrooms, check the attic, check the basement, check the dehumidifier, walk out.

The wrong answer is vague: "I make sure everything's good." A caretaker who can't articulate what they do is a caretaker who isn't doing it consistently.

3. What do I receive after each visit?

This is the question that separates the professional caretakers from the rest of the field. The professional answer is: a written report, with photos, after every visit, sent to you within a defined window (most are same-day or next-day). The vague answer is: "I'll text if there's a problem."

A caretaker who only contacts you when there's a problem is a caretaker you cannot evaluate. You don't know if they visited. You don't know what they checked. You don't know if the smoke detectors got tested last month. The whole point of caretaking from a thousand miles away is the documentation. If there's no documentation, you're paying for visits you can't verify.

The best caretakers on the island send a structured report after every visit. Some hand-type. Some use property management software. Some dictate their findings into voice notes that get turned into structured reports automatically. The format matters less than the consistency.

4. How do you handle storms?

This is where Nantucket caretaking diverges from caretaking anywhere else. The right answer breaks the question into three parts:

• Pre-storm: outdoor furniture stowed, generators fueled, water mains verified, owner notified.
• During storm: drive-by checks if conditions allow, monitoring of any property-specific risks (low-lying houses near Hummock Pond, exposed beachfront properties, anything with mature tree cover).
• Post-storm: full walkthrough within 24 hours of conditions clearing, with documentation of any damage and immediate temporary protection where needed.

If the answer to "how do you handle storms" is "I'll take care of it," ask for the breakdown. The good caretakers have a procedure.

5. Who are your trusted vendors?

The caretaker's value isn't just what they do themselves. It's the network they bring with them. A good caretaker on Nantucket has a roofer they trust, an electrician they trust, a plumber they trust, an HVAC tech they trust, a chimney sweep, an exterminator, a window company, an arborist. They have these people on speed-dial because they've used them on dozens of properties and know their work.

When you ask, the answer should be specific. Names. Companies. Years they've worked together. A caretaker who hesitates here is a caretaker who'll hire whoever's available, which is not always who's good.

6. How do vendors work with you on my property?

Two patterns:

The strong pattern: vendors arrive at your property, the caretaker meets them or has briefed them, the work is done, the caretaker walks the work afterward, the vendor's invoice goes to the caretaker who reviews it, then to you with the caretaker's notes.

The weak pattern: vendors arrive, do whatever, leave, send you an invoice that you have no way to evaluate.

The first pattern means you have someone on your side who is reviewing the vendor's work. The second pattern means you're getting whatever the vendor decides to charge for whatever they decide they did.

7. How do you handle keys, alarm codes, and access?

Sounds boring; matters enormously. Ask:

• Who has keys to my property? (The caretaker themselves; their partner or backup; sometimes a trusted vendor or two.)
• How are keys stored? (Lockboxes off-site, indexed; not "in my truck.")
• What's the alarm protocol? (Codes tracked centrally; alarm company has the caretaker as a contact; protocol for false alarms.)
• What's the protocol if you're unreachable? (Backup person; documented; you have their number.)

A caretaker who can't answer these crisply is a caretaker who has lost a key before.

8. How do you handle off-island periods or vacation?

Even the best caretakers go on vacation. They have backup. The right answer is: "I have a partner who covers when I'm away. They're briefed on every property. The schedule and any active issues get handed off." The wrong answer is hand-waving about how it never really happens.

Ask: does the partner send the same kind of weekly reports? In the same format? Or does coverage mean visits stop being documented for two weeks?

9. What's your background?

Some Nantucket caretakers are former contractors who shifted into property care. Some are from the trades — plumbers, electricians, builders — who pivoted. Some come from hospitality (running estates, working for high-net-worth families). Each background brings different strengths.

What you want to hear is a coherent story that explains why they know how to walk a house and what to look for. A caretaker who came up doing rough carpentry knows what a structural issue looks like. A caretaker who came up doing fine residential remodels knows what a finish issue looks like. A caretaker from estate management knows how to coordinate vendors. The best ones have spent enough time across categories to read a house broadly.

10. What's your insurance?

Caretakers should carry, at minimum:

• General liability (typically $1M per occurrence, $2M aggregate).
• Workers' comp if they have employees.
• Commercial auto on their work vehicles.
• Sometimes errors-and-omissions or care-custody-and-control coverage, depending on the scope.

Ask for a certificate of insurance naming you as additional insured if the contract is large or the property is high-value. Any professional caretaker will provide this without friction.

11. How do you handle owner communication?

A spectrum:

• Reactive only: texts when there's a problem.
• Reactive plus monthly: texts on issues, monthly summary.
• Visit-by-visit reports: structured documentation after each visit, plus immediate communication on issues.

The third is the standard you should expect on a high-value second home. Some caretakers will charge a premium for this level of documentation; it's worth paying for.

You should also ask about response time on a non-emergency: when you email a question on a Tuesday afternoon, when do they typically respond? "Within 24 hours" is reasonable. "By the end of the week" is not.

12. Why are you taking on a new client?

This is the most important question and the one most owners forget to ask. The good caretakers are full. If they're taking new clients, there's a reason. Sometimes it's growth (new partner, expanded capacity). Sometimes it's churn (a previous client moved on). Occasionally it's something less flattering — they lost a property because they messed up, or they're overextending capacity to chase revenue.

The honest answer is informative either way. A caretaker who has expanded to support a new partner is in growth mode and might be a great long-term match. A caretaker who's just lost a property because of a service failure is a risk you should price in.

What good documentation looks like, in practice

Once you've hired your caretaker, the test of whether they're worth the money is the documentation pattern that gets established. Here's what good looks like, from an owner's perspective:

• Weekly emails containing a structured visit report. Not a paragraph; not "all good." A proper report with sections.
• Photos of the thermostat reading, the boiler, the basement. These take 30 seconds to capture during the walk-through and are the simplest proof of presence and condition.
• Issues called out promptly, with a recommendation. Not just "your roof has a problem"; a description of what they saw, an estimate of urgency, and a proposed next step.
• A monthly or quarterly summary that aggregates the visits, lists work done, work pending, vendors used, and costs.
• A storm-response report within 24 hours of any major weather event, even if the property is fine. The absence of damage is itself worth documenting.

Some caretakers produce this with a notebook, a folder of photos, and a Sunday-night session typing it all up. Some use property management software. Some dictate it in the truck after each visit and let a tool turn the dictation into a structured report.

The medium matters less than the consistency. What you want, as an owner, is the ability to open up a folder six months from now and see exactly what happened at your property every week of the off-season.

The unstated answer

The implicit question behind every other question: can I trust this person with the most expensive thing I own, when I'm not there to check on it?

The honest answer is that trust is built over a year. The first season tells you whether they show up on time, communicate clearly, document consistently, and handle the small problems without involving you. The second season tells you whether they handle the larger problems — the burst pipe at 2 AM, the storm damage, the contractor dispute — with the same consistency.

The questions in this guide help you screen for the kind of person who's likely to pass that test. The actual test happens over time. Hire carefully, set the expectations clearly, and pay attention to the documentation pattern over the first six months. By the time the next off-season starts, you'll know whether you've found the right one.