Redeveloping the former Monoco Oil site at 75 Monroe Avenue in the Village of Pittsford was never going to be an easy task.

The site's industrial history meant that complex and expensive cleanup work would be necessary before it could be reused. And its location at a major gateway into the village meant that any proposed development would be heavily scrutinized.

A Mark IV Development-affiliated company, Pittsford Canalside Properties, purchased the property a few years ago and it's now deep into the cleanup work; it has removed 48,000 tons of potentially contaminated soil from the site, says the state Department of Environmental Conservation.

Chris DiMarzo, Mark IV's chief operating officer, says the company has invested millions of dollars into the cleanup.

But Mark IV wouldn't invest that kind of money if it didn't expect the site to pay off down the line. Ultimately, the development company wants to build 167 apartment units and a restaurant on the site; they call the project Westport Crossing.

But there's a problem: many residents and some village officials say the project doesn't fit with Pittsford's architectural and historic character. They object to the size of the buildings and the project's layout.

As a result of the controversy, the project is advancing in something of an uneasy state. The developer continues to pursue the village and state approvals it needs, but at the same time, two court cases have the potential to alter the project's trajectory.

"It's a pretty complicated scenario all around," says Pittsford Mayor Bob Corby.

The problems started after a November 2012 decision by the village board to issue special permits for the project — a decision that split board members. (Corby and former board member Paula Sherwood voted against the permits. They said the plan didn't fit the village's character.)

Ultimately, a citizens' group filed a lawsuit challenging the special permit approvals. A subsequent approval by the village planning board led to the second lawsuit, when the developer filed to try to stop an appeal of the planning board's decision.

Monroe County Supreme Court Justice John Ark will hear arguments in both cases on December 12. Decisions probably won't come right away.

Mark IV's DiMarzo says the village board's original decision to issue the special permits is sound. And the company still expects to have final approvals for its plans within a few months, to break ground on the project this spring, and to have the new buildings occupied in 2015, he says.

"I am confident that the village leadership acted professionally and made their decision with all of the facts in front of them," DiMarzo says.

The Friends of Pittsford Village citizens' group is behind the lawsuit to get the special permits for Westport Crossing annulled. But the case's details have less to do with the actual project than how the village board made its decision to approve the permits.

Alan Knauf, the group's attorney, says the board met with the developer in closed sessions to discuss financial aspects of the project. The developer presented the financial information to justify the number of apartment units in the project, he says.

But many of the residents' concerns and objections — especially traffic impacts and architectural compatibility — stem directly from the project's size. Since village board members considered the financial information as they decided whether to approve the special permits, Knauf says, the public should have been able to review and comment on that information.

But village officials withheld it, arguing that making the information public could have damaged Mark IV professionally, says the lawsuit.

A ruling in favor of the Friends group could mean that Pittsford Canalside Properties has to reapply for the special permits. It could also render the other pending lawsuit moot, Knauf says.

The village planning board approved the developer's preliminary site plan in July, which was the next big step for the project after receiving the special permits. But that action set the stage for the second legal challenge.

At the heart of the lawsuit is a village law that lets any "applicant or interested person" appeal a planning board decision via the village Board of Trustees. And one week after the planning board approved Westport Crossing's preliminary site plan, Friends of Pittsford Village and two residents, Justin Vlietstra and Michael Reynolds, filed an appeal.

They say the plan approved by the planning board varies too much from the plan approved by the village board in that the developer moved and enlarged buildings and changed the site's layout. The permits regulate certain aspects of the project, including placing restrictions on the number and size of buildings.

In response, Pittsford Canalside Properties is suing the village to prevent it from applying the local law allowing the appeal. The company is also asking the judge to strike down the law, arguing that state law, which lays out a process for residents to challenge a board decision in court, overrides the local law.

If Justice John Ark does rule on this lawsuit and sides with the developer, the decision may prevent future local-level appeals in Pittsford.

But it could also add another complication — and more tension — to the situation with Westport Crossing. Mayor Corby and some members of the village board say that the plan approved by the planning board doesn't meet the criteria established by the village board, and that the developer is in violation of its permits.

So if Pittsford Canalside Properties prevails in court, the village board could end up suing the planning board, Corby says.

The project also needs additional approvals from the village board, Corby says, including the extension of a sewer district.

"I can't imagine that we would approve expanding the sewer district to facilitate a project that is in violation of our own special permit," Corby says.

And Knauf says his clients, Friends of Pittsford Village, may sue if the site plan receives final approval, which is the next step in the village approval processes.

"When and if that happens, we can respond to that," DiMarzo says

The developer is scheduled to appear before the village board on December 16 for final site plan review.