When he departs for a new job in Wareham this summer, Vineyard schools superintendent Dr. Matthew D’Andrea will leave behind a school system facing challenges on multiple fronts.

“We’re in negotiations with the teachers union, which has moved to mediation, [and] we’re trying very hard to make sure that we get to contract negotiations with the custodians and the food service workers, because their contracts end in June,” all-Island school committee chairman Kate DeVane told the Gazette this week.

In addition, the fate of a new or significantly rebuilt high school rests on whether all six Island towns can agree on a capital spending formula in order to qualify for up to 38 per cent in reimbursements from the Massachusetts School Building Authority.

Mr. D’Andrea is the sole school district employee named to the new, Islandwide ad hoc committee charged with arriving at the capital funding formula. The group, composed otherwise of elected officials and town administrators from all six municipalities, held its first meeting Wednesday night.

The Wareham school committee voted unanimously April 14 to select Mr. D’Andrea, a former Wareham teacher and principal as its next superintendent of schools.

And while he has not yet signed a contract, Mr. D’Andrea said his start date in Wareham is July 1.

Given all these irons already in the fire and the additional challenges that would be added by a search to replace Mr. D’Andrea, Ms. DeVane said, she would rather see assistant schools superintendent Richie Smith take over the top job.

“There are lots and lots of things going on, which I think makes it important to have some level of continuity of leadership,” Ms. DeVane said. “I would like to see Richie in that spot.”

She emphasized however that no decision can be made until the committee discusses the matter, likely in a meeting next week that has not yet been posted.

“Everything is in play until we meet,” Ms. Devane said.

Mr. Smith, formerly principal of the Oak Bluffs School and before that principal at the Tisbury School, was the other finalist for the top Vineyard job in 2015, when Mr. D’Andrea was chosen to succeed retiring schools chief James Weiss. Mr. Smith became assistant superintendent the same year.

“Building the high school is going to take three years,” Ms. DeVane added. “Maybe what we do is some sort of prolonged interim position.”

Another reason not to immediately begin a search, Ms. DeVane said, is that the all-Island school committee is not a unified body.

“We have not been pulling in the same direction for a while now,” she said. “The main thing I’m really concerned about is that we come together as a group, smoothly, to solve the problem . . . What we have to do is get together as a school committee and really decide what’s the best next move for the school [district] in general.”

The superintendent’s departure will

leave the Vineyard in its final stages of qualifying for MSBA funding for the high school — a perennial quest for Mr. D’Andrea, who shepherded the district through six years of applications before earning a conditional pledge this year of up to 38 per cent in qualified reimbursements from the state school building authority.

But while he will not preside over the long-awaited construction project, Mr. D’Andrea can claim other accomplishments during his Island tenure, Ms. DeVane said.

“Matt did some really great things while he was here,” she said, citing improvements in both traditional English classes for native speakers and language classes for English learners.

“He used to be a teacher [and] he has a focus that is very much the educational viewpoint, and I think he did that really well.”

Ms. DeVane also praised Mr. D’Andrea’s efforts to calm the roiling political waters of the Island’s assorted, overlapping district committees.

“He came into this extremely contentious time on the Martha’s Vineyard school committees where they were very divided and very hard to work with, and he tried very hard to do that,” she said.

And Mr. D’Andrea also showed strong leadership in the face of the Covid-19 pandemic, Ms. DeVane said.

“Hands down, I think he probably had one of the best Covid response programs in the state,” she said.

“I’m aware a lot of people weren’t happy with it, [but] he just did a very good job of navigating all that . . . The testing he put in place the first year made it possible for us to go back a lot sooner,” Ms. DeVane added.

Amy Houghton, who chairs both the regional high school committee and the Tisbury School committee, echoed Ms. DeVane’s appreciation.

“I wish Matt all the best,” Ms. Houghton told the Gazette by phone last week. “I think he was a great support to staff and students and families during a very difficult number of years. And we will miss him.”

Mr. D’Andrea expressed mutual feelings in a phone call with the Gazette.

“The Island is a wonderful community  — I’ll always feel a connection to it,” he said.