This story is part of a collaboration with the Martha’s Vineyard Times and reporter
Sarah Shaw Dawson
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
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

Fynbo, who bought his home 40 years ago for $86,000, said the best his agent could find was a
bare-bones policy
“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
On the island, the
nonrenewal rate spiked
“It’s a
bad situation

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
“Fortunately I have something,” she said, “but it’s definitely not ideal.”
The
Mass Fair Plan
“There are big deductibles,” Orazem said. “And if it’s a named storm I’ll be paying more.”
A “
named storm
“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

“I know there are some risks in not having it,” McGhee explained. “
It was costly
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
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
“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
Copyright 2025 CAI