A residential and commercial development in Bayside that was scaled down to head off a lawsuit has run into new resistance from Portland’s Planning Board.

The board on Tuesday directed city staff to work with the Miami-based developer to come up with a better design for four six-story buildings along Somerset Street, a project known as “midtown.” However, the board’s request for an extended review could jeopardize the compromise and again cast uncertainty over a project that has been in the works for nearly five years.

Some of the issues raised this week include traffic management, drainage, exterior materials and a particularly large building proposed near Trader Joe’s on the western portion of the property, said Jeff Levine, the city’s director of planning and urban development.

The directive comes nearly a year after the board approved Federated Cos.’ initial master plan for four, 14-story high-rise buildings and approved construction of the first phase, including one tower and a parking garage. A group of residents, calling themselves Keep Portland Livable, challenged that project in court and tried to overturn the city’s approval.

In October, Federated Cos. presented a scaled-down plan as part of an agreement with the opponents to suspend the lawsuit. That led to the latest review by the Planning Board.

The revised plan calls for four six-story buildings, reducing the maximum height from 165 feet to 72 feet and the number of market-rate apartments from 650 to 445. Only one parking garage would be built, instead of two.

Planning Board Chairman Stuart O’Brien said Thursday that members must consider the new proposal on a more technical level because Federated is seeking site plan approvals to begin building the entire project in 2015, rather than present the overall project in phases as originally planned.

“The process is different. We’re looking at different things in different ways,” O’Brien said. “There is a lot of detail we didn’t address before that we need to work through now.”

Federated Cos. wanted the Planning Board to hold a public hearing and vote on the project in January. But the board wants to conduct a series of workshops to address the lingering issues.

“It’s a very large project,” Levine said. “I think (board members) definitely want to see some more information from the developer. They’re particularly interested in making sure architecturally it makes a positive statement. If the developer is willing to make adjustments to their plan, I don’t think it’s a huge hurdle at all.”

Jonathan Cox, founder and chairman of Federated Cos., declined to comment on the current planning process.

“We feel this is a really strong project,” Cox said. “We think the project in many respects is better than the previous submission.”

City Urban Designer Caitlin Cameron said in a Dec. 1 memo to the board that planners do not support “materials such as vinyl or EIFS,” which stands for exterior insulation and finish system. Levine said in an interview that the exterior building material looks like stucco and its durability in cold climates is questionable.

Cameron also criticized the length and design of Building 3 planned for the western side of Somerset Street, near Trader Joe’s.

“Currently, there is not enough variation in the program or design of the building to provide a varied and enjoyable pedestrian experience,” Cameron wrote. “The building overall is monotonous and lacks an authentic variation in massing, articulation and materiality.”

Tuesday’s meeting was the second workshop the board has held on the project. Each meeting was lightly attended by the public, which stands in stark contrast to previous public meetings focusing on the initial high-rise plan. The two public hearings leading up to the board’s January approvals drew nearly 100 people to testify both in support of and opposition to the project, which had been in the city review process for two years.

Conspicuously absent this time around is Keep Portland Livable, a loosely organized group that challenged the original project approval in court on the basis that the project violated the city’s comprehensive plan.

Peter Monro, the group’s co-founder, said the group agreed to not formally oppose the new design’s building height, footprint and form at the Planning Board level and to not challenge any approvals in court. Members of the group, including Monro, could speak as individuals, but even that has not occurred.

“There was the sense from those who are involved with Keep Portland Livable that the new design achieves some of the fundamental goals we set out to achieve,” Monro said.

The group has put a hold on the lawsuit until Jan. 16, 2015, according to a motion and memorandum filed Oct. 7 in Superior Court. It’s not clear what would happen if the new plan is not approved by that date.

The motion, which lists the city, Federated and Legacy Park Apartments as defendants, states that the discussions between Keep Portland Livable and the Federated defendants addressed the developer’s need to have “certainty as to the timing of the development and the resultant need to acquire final approvals within an identified schedule.”

Although the motion notes that the project changes require Planning Board approval, it also says: “Counsel for plaintiffs and for Defendant City of Portland have consented to this motion.”

However, Portland Communications Director Jessica Grondin said the city was not a party to the agreement between Federated and Keep Portland Livable.

Also, in an Oct. 17 letter to Monro, Levine, the planning director, reiterated that city staff could not guarantee board approvals of the new project.

“As you know, we are certainly not in a position to speculate about the Planning Board’s decision at this early date, nor do we have any control over that board’s ultimate decision,” he wrote.

If the board rejects the compromise proposal, Federated Cos. could still pursue the larger development plan through the courts.

The project is planned for 3.25 acres that are owned by the city, which marketed the property for large-scale residential and commercial development. Economic Development Director Greg Mitchell said Federated, which entered into a purchase-and-sale agreement in May 2010, has not yet closed on the $2.4 million sale because the project is in limbo.