This story is part of a collaboration with the Martha’s Vineyard Times and reporter Sarah Shaw Dawson. The Times’ reporting on homeowners insurance can be found at mvtimes.com.
Faced with the threatened loss of his home insurance, lifelong Chappaquiddick resident Bob Fynbo spent $70,000 last year to fix his roof. He didn’t think it was in bad shape – and a building inspector wrote a letter saying as much – but his insurance company disagreed.
“They still wouldn't touch it,” Fynbo said. “So I did all that. Everything they asked for.”
It was a massive sum for the 65-year-old engineer, who operates a wifi tower in the tiny island community off Martha’s Vineyard that boasts about 250 year-round residents. But Fynbo’s mortgage requires that he maintain home insurance, and he figured that the repairs would keep his policy cost at the same annual rate of about $3,200, already double the average for Massachusetts homeowners.
But then, last spring, after paying for the new roof and spending another $30,000 for shingles on the outside of the house, the renewal notice arrived from his insurer.
“When they came back with the quote of $11,900, it was like a gut punch,” Fynbo said. “I just sat there and stared at it going, ‘Sorry, what?’”
Baffled by the 360 percent increase, Fynbo and his insurance agent scrambled to find another option for his home, which is almost a mile from the ocean. But the insurance industry is doubling down on a bet that climate change will soon bring catastrophic storms to the island, producing unprecedented damage.

Fynbo, who bought his home 40 years ago for $86,000, said the best his agent could find was a bare-bones policy for almost $6,000 a year, double his previous premium. The ordeal is giving him a familiar sense of dread that he could lose it all.
“I was born in southern Minnesota, and when I was 8 years old, our farm got destroyed by tornadoes. And we lost everything,” he said. “My toys, my clothes, there was nothing left. And that feeling of helpless[ness] in the situation came right back for this…. It's like, ‘Okay, so I've worked for all of this stuff. And I might not be able to keep it at the rate things are going.’”
Today, Fynbo is one of many islanders facing terrible choices because of the soaring costs of home insurance. In a Martha’s Vineyard Times survey on the topic that yielded roughly 300 detailed responses, Vineyarders shared that they were delaying retirement; or avoiding knee replacement surgery; or skipping meals with friends; or debating a move off island for good. All the while, they’re praying that next year the rates won’t jump even higher or that they won’t get dropped by insurance companies altogether.
On the island, the nonrenewal rate spiked from less than half a percent in 2018 to nearly 12% in 2023. In fact, Martha’s Vineyard has seen the third-highest rate of dropped homeowners’ insurance of any community in the country, according to a report from a U.S. Senate advisory committee. And the community isn’t alone: One recent study showed that insurance firms increased the percentage of nonrenewals in 35 states between 2018 and 2023.
“It’s a bad situation,” said Edgartown resident Deb Mello Orazem. “And I don’t even – I’m sort of shallow breathing now.”

In September, Orazem, who taught in island schools for 27 years, learned that her insurance provider was dropping her. A different insurance company would only cover her home if she paid $9,000 a year. On her fixed income, it became clear that what the private market had to offer was out of reach. So Orazem is now among the 200,000 Massachusetts policy-holders who rely on the Mass Fair Plan, a state-mandated insurance program. About 102,000 of them live in Barnstable, Dukes, or Nantucket counties.
“Fortunately I have something,” she said, “but it's definitely not ideal.”
The Mass Fair Plan acts as a so-called “market of last resort” for Bay State residents to secure a mortgage and stay insured since 1968. But FAIR plan policies can leave many underinsured. For instance, those policies only cover up to $1 million in replacement costs, which is plenty to rebuild almost anywhere, but not necessarily on Martha’s Vineyard, where even a modest new-build can cost more. And that’s not the only drawback.
“There are big deductibles,” Orazem said. “And if it's a named storm I'll be paying more.”
A “named storm” refers to a hurricane or nor’easter that’s big enough to become a “Bob” or a “Sandy.” Some islanders, facing sky-high insurance policies, are opting to go without protection from these major weather events.
“We have no coverage for named storms. So I presume if there was damage, we would be solely responsible for it,” said Chilmark resident Peter McGhee.
McGhee, who is a former WGBH employee, made the decision to drop named storm coverage after he saw his policy jump 50% in a single year to $6,000. Without it, his policy is around $1,500 per year, he said.

“I know there are some risks in not having it,” McGhee explained. “It was costly and it was that the increment of cost didn't seem to be warranted by the probability of damage.”
McGhee considered a few facts: his home doesn’t carry a mortgage, it’s about a mile back from the ocean, and, at 90, he’s seen hurricanes. None, he said, has ever taken a single shingle off his home or the home next door. Still, he knows his luck might not hold. “I have to acknowledge that with climate change, it's bruited about that there is greater risk of hurricanes our way,” McGhee said.
For Chappaquiddick resident Bob Fynbo, who spent decades volunteering as a firefighter, EMT, and one-time candidate for local office, the future is uncertain.
He now has a new roof over his head but no sense of security as he faces a question: can he afford the insurance that’s now his largest expense or, does he need to leave behind the community he’s known for the last six decades?
“I'm coming up on an untenable choice. You know, which do I do? Do I move and – ,” he trailed off. “I don't see where this comes out good for me. I only see where it just keeps whittling me down and down so that all the effort I put in to get to where I am becomes valueless. And that's heartbreaking.”
Fynbo’s policy will face renewal in April. The clock is ticking.