Jim Reynolds came to Martha’s Vineyard looking for a simpler, quieter life. Ron Rappaport, born and raised in Oak Bluffs, came back for the same thing.

The two men are pretty different. Mr. Reynolds is quiet and measured in a crisp white shirt. Mr. Rappaport is scrappy and demonstrative with finger-in-the-light-socket hair. They first met 30 years ago and something just clicked. Brought together by their mutual friend Dennis da Rosa for dinner at the Home Port in Menemsha, the conversation turned to a partnership.

“Started talking about setting up our own firm,” Mr. Rappaport said. “One thing led to another, and we did it. And then we bought a building together. They were both scary. It was something we did 30 years ago. We probably wouldn’t have the courage to do that today.” This week their firm, Reynolds, Rappaport, Kaplan & Hackney (Fain Hackney was added as a named partner later) threw a party on the front lawn of their Cooke street offices to celebrate 30 years of lawyering and 30 years of community friendship.

“We get to live in this lovely place,” Mr. Reynolds said. “I could not have taken a blank slate and written a more ideal scenario for myself as a professional.”

When they began, there were three lawyers, including Mr. Rappaport’s wife Jane Kaplan, two assistants and a business manager. Both men say one of their proudest accomplishments is that all the original employees are still with the firm, with the exception of an assistant who retired last year. Now the firm employs 10 attorneys and 10 other people in paralegal and support positions. Mr. Reynolds and Mr. Rappaport describe their staff in glowing terms, using words like ace, talented, remarkable, excellent and superstar.

Little has worked out badly for the two founding partners, but little has worked out as they expected.

Mr. Rappaport and his wife were both partners in high-octane Boston law firms when their daughter Julia was born. Ms. Kaplan took six months off, and then another six months off. The couple couldn’t see a way to merge the demands of parenthood with the all-consuming legal profession. Eventually they decided to give up secure jobs and the salaries that came with them.

“We decided that we would try to create our own law firm, where we could set our own hours,” Mr. Rappaport said. “I thought it was going to be more of a boring, mundane, legal practice with more family time. The surprise has been our cases have been complicated, interesting, fascinating, stimulating. Frankly, I’ve worked just as hard here as I did in Boston. The idea of getting more family time didn’t really work out the way I envisioned it. ”

Mr. Rappaport’s practice has focused on municipal law. He is the town counsel for all the Island towns except Tisbury. His work ranges from small to large. He vets town meeting warrants and helps town police departments when they need to buy a cruiser. He defended Edgartown’s interests in a land use case that challenged three-acre zoning, lasted two decades and went all the way to the Massachusetts Supreme Judicial Court. The town won the case.

While his first response to a legal dispute is to find a creative solution without going to court, Mr. Rappaport’s legal opponents know litigation is not an empty threat.

“No one likes to spend money on lawyers,” he said. “When it comes to public entities, your legal fees are voted on every year by the voters. But you can’t back away from a fight, and you can’t compromise anybody’s rights, particularly public rights. If something needs to be defended and I can’t work out a resolution, I’m going to trial.”

Mr. Reynolds also was drawn to Martha’s Vineyard as an exit off the fast lane. He arrived on the Island in 1976, practicing for 10 years before joining forces with Mr. Rappaport.

He remembers well that dinner at the Home Port in 1986.

“As we talked, I think we realized we shared a common vision, common set of ambitions for what a law firm could look like, which would be a little different,” Mr. Reynolds said. “So we threw our hats in together.”

His work has focused on real estate law, guiding clients through high-end property purchases, sorting out disagreements over titles and easements, negotiating mortgages and contingency clauses.

“You’ve got to find common ground between people,” Mr. Reynolds said. “You have to figure a way to broker a solution. Someone may not want an easement over this portion of his property. Does the easement stay in one place for limited time and then gradually move to a different location? There’s a sense of creativity to it.”

Mr. Reynolds said he didn’t anticipate the accomplished clients the firm has worked for over the years, or the important cases the firm took on.

“I don’t think there’s any way, no way I could have predicted how our practice would evolve. The Vineyard was a very different place when I came,” he said. “What the Vineyard has become since is something I couldn’t have imagined. With it has come a lot of challenges and interesting work. I find myself in complex situations that I may not have seen before and I really need to solve the problem the client is presenting. Our clients are terrifically sophisticated. These people are so bright and they engage me so actively in the transaction it really keeps me on my toes.”

Asked to describe each other’s best qualities as an attorney, the two founding partners demonstrated the deep respect, on personal and professional levels, they hold for each other. There is little doubt who they would want in a foxhole with them.

“His intellect,” said Mr. Reynolds, speaking about Mr. Rappaport. “He’s tough. If he has to try a case and he believes in an issue, he’s going to fight you to the very end.”

“Jim is an incredibly thorough lawyer,” Mr. Rapport said. “It’s a great trait. He brings a passion and thoroughness for detail that is pretty remarkable.”

There have been surprises, triumphs, financial rewards, and few disappointments in 30 years of practicing law together. One thing it has never been is boring.

“I never thought I would come into contact with such a range of talented, interesting people,” Mr. Rappaport said. “We have a lot of characters here, and it enriches the practice.”