On Tuesday night, in the early days of summer vacation, upcoming senior Kevin Segal sat in the gymnasium of Portland’s Hall Elementary School with his face buried in one hand.

He was frustrated, fidgeting with his name tag.

As the Board of Education meeting over whether to urge Portland to borrow $70 million in bonds to fund much-needed repair and renovation of four city elementary schools entered its third hour, the 17-year-old student representative for Portland Arts and Technology High School slumped in his chair, impatient with the pace of municipal governance.

“This is the perfect example of the grinding wheels of bureaucracy,” Segal told the room. “We need to vote on this.”

The school board did end up passing the recommendation, kicking it up to Portland’s City Council, which will determine whether to put the question to voters as a ballot issue in November.

But this isn’t the first time the board has recommended upgrades to the schools. Portland’s elementary schools have faced many of the same challenges since long before Segal was born.

Tuesday’s vote represents the seventh concerted effort since the mid-1990s to improve facilities at Portland’s older elementary schools, which have not had major renovations since they were built 55 to 65 years ago.

Between 1994 and 2013, according to a school district timeline of facilities work, Portland has formed task forces and hired architecture firms to develop plans for how to improve the facilities of the city’s aging elementary schools six separate times — and yet many infrastructure issues that have plagued the schools for decades persist today.

In 2013, the board unanimously passed a bond proposal for renovations at the same elementary schools based on a $700,000 study commissioned from an architecture firm.

That proposal never made it out of committee — partly because councilors wanted to prioritize renovating Hall Elementary School, but it was unclear whether state funding would be available for the project billed at nearly $30 million. (The spending for the rebuilding of that school was finally approved in April.)

Segal was not alone in his impatience to see action on the conditions at the Presumpscot, Longfellow, Reiche and Lyseth schools. Board members who remember that last struggle over the issue — and the one before that — say a fix is long past due.

The problems described by parents and students at the school board meeting and in the most recent review by architecture firm, Oak Point Associates, vary by school. At Lyseth and Presumpscot, which serves many of Portland’s lower-income students, mobile trailers intended as a temporary solution to create more classroom space have become a permanent fixture. At Reiche, on the West End, the roof leaks and classrooms are overcrowded. And at Longfellow, there isn’t enough space for special education classes, and the same room serves as both gym and cafeteria.

[MORE: The Hall School needs serious work. But so do these other 4 Portland schools]

This year, state funding was secured to cover 95 percent of a $29.7 million bond to revamp old facilities at Hall Elementary — and Oak Point was re-hired to revise its initial study to address the four other elementary schools.

According to city councilor Justin Costa, the long-standing challenge in finding funds to renovate the elementary schools is tied to both the availability money from the state and how the city managed its long-term infrastructure investments.

Costa, who served on the school board during the 2013 bond proposal, said that recent restructuring of how the city finances major projects creates new possibility for a locally funded bond. But other veteran school board members are concerned that the Council is unlikely to approve the plan similar to the one it shot down three years ago, especially as it would require tax increases.

Just days before Tuesday’s vote, board member Sarah Thompson, the who was chairwoman in 2013, proposed an alternative plan that would cut the bond nearly in half, from $70 to $40 million — suggesting that would be better than nothing. And faced with the prospect of returning to the Council with a $70 million bond proposal, board chair Marnie Morrione, who also served in 2013, said she would strongly advocate for it but also quoted an often-cited definition of insanity: “Doing the same thing over and over again and expecting different results.”

Some city councilors are signalling that these concerns are well founded.

Councilor Nicholas Mavodones, the chairman of the City Council’s finance committee, said that he was open to the idea, but doubted that there was a fiscally responsible way to advance the $70 million bond proposal, which would require an estimated 1 to 1.5 percent tax increase on residents for the first five years.

He also suggested that it would be difficult for the Council complete its vetting of the proposal to meet the deadline to have the measure placed on the November ballot.

“There’s not a lot of time between now and August to address this issue,” said Mavodones. “It’s unfortunate that it’s coming to us at the end of June.”

But many students, parents and political leaders believe the condition of some of Portland’s elementary school has deteriorated to the point that students in the schools that need renovation are not receiving an equal education.

“For decades we’ve studied our schools and for decades we have found our schools are unequal,” said Mayor Ethan Strimling on Tuesday. “That’s amoral on out part.”

Costa said that a failure to act on the schools now will only make the problem harder to fix later.

“The risk of delay is that ultimately we just force ourselves into paying higher construction costs and interest rates down the line,” Costa said. “It’s going to be increasingly difficult to keep families in Portland if our school buildings look like they’re from the ‘50s and ‘60s.”