As Melvin Cherry Jr., watched the vacant houses next door to his family home fall into disrepair, he came upon what he thought was a simple solution: His family could buy them from the city and fix them.

Now, more than 2½ years after Mr. Cherry’s parents applied to buy them, the houses continue to deteriorate, with overgrown weeds and loiterers contributing to safety concerns. The city refused to sell the properties on Bryn Mawr Road to the Cherry family, instead agreeing to convey them to the Urban Redevelopment Authority, which has not yet taken ownership or improved them.

“Why do you have to live around blight when you have potential buyers who will fix up the properties?” said Mr. Cherry, a lifetime resident of the Hill District who works at the University of Pittsburgh’s School of Social Work.

Mr. Cherry and his family are among hundreds of would-be buyers who have experienced the prolonged, convoluted and sometimes arbitrary process of acquiring a city-owned property. For a variety of reasons — from URA intervention to city council’s full discretion to cancel a sale without explanation — prospective buyers face uphill battles to acquire blighted properties.

An analysis conducted by the Post-Gazette found that of 1,479 applications filed by individuals and private businesses between mid-2015 and mid-2018 for city-owned homes and lots, only 25 resulted in the publicly recorded sale of the requested property to the applicant by June 2019. The average length of the process for those successful applicants was about two years, four months.

“The worst enemy of a tax-delinquent, vacant, abandoned property is time,” said Kim Graziani, a former Pittsburgh official who is now vice president and director of national technical assistance for the Michigan-based Center for Community Progress. “The more time that passes where that property has no responsible owner,” she said, the more likely taxpayers have to pay “to send police, to send fire trucks, to send the board-up crew to board up property” — or, ultimately, to demolish it.

The property sales process came under scrutiny last year after the Pittsburgh Post-Gazette reported that the city’s real estate director, Aaron Pickett, sold himself a city-owned vacant home for $2,500. The state ethics committee this month announced that Mr. Pickett violated the Public Official and Employee Ethics Act and must pay a $5,000 fine.

A year ago, city leaders promised more transparency and a faster process for individuals seeking to buy vacant properties through the treasurer’s sale process. At the time, city treasurer and finance director Margaret Lanier said cutting the process down to nine to 12 months would be optimal for the city, although she clarified this month that 18 months would be a more reasonable goal.

Little evidence exists that significant improvements have occurred, especially regarding the sale of city-owned abandoned houses, which tend to cause more concern for neighbors than do empty lots.

The city’s property sale “process is kind of stuck in the 1980s,” said Joseph Schilling, a senior research associate with the Washington, D.C.-based Urban Institute, whose specialty is vacant property. “The downside is that that property is still either underused or vacant and abandoned, and that has negative costs and impacts to the surrounding property owners, the residents,” from decreased property values to increased criminality and the “mental setback” to the neighborhood.

The city and its agencies are “not good neighbors,” said city Controller Michael Lamb. “What we have right now is a mess out there.”

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The five-month background check

The city took ownership of the two abandoned, tax-delinquent houses beside the Cherry family’s home in April 2016.

That hasn’t yet led to improvement.

This year a group of teenagers began to use the porch of one of the vacant homes to smoke marijuana, Mr. Cherry said. He shooed them away, but he said he remains concerned about his family’s safety, especially that of his teenage daughter.

According to Mr. Cherry’s wife, Latonia, the city has yet to cut the grass this summer, a complaint echoed by dozens of families across the city who live near city-owned lots.

“When you come home and get out of the car, you don’t want to look at that,” Ms. Cherry said. “There is trash all over that house and the vines are now on our yard. … We don’t allow the kids to play in our backyard anymore.”

Mr. Cherry helped his parents submit an application to buy the properties on Bryn Mawr Road in January 2017. The application states that Mr. Cherry’s father hoped to “restore” the houses “to be used by a family member.”

After receiving the application, the city’s Real Estate Division took more than five months to assure that Mr. Cherry’s father did not owe any back taxes or water and sewage bills in order to approve him as an eligible buyer.

That modest background check almost always adds four months or more to the purchasing process. In 2017, the Real Estate Division approved would-be buyers within 120 days in only 12% of cases, according to Mr. Lamb, whose office is finalizing an audit of city property sales from 2015 through 2017. That was down from 19% in 2016 and 64% in 2015.

Ms. Lanier said the process slowed down because the city had no sales coordinator during most of 2016, and also began to involve the URA in setting property prices.

Some eligibility decisions, Mr. Lamb noted, took as long as nine months.

A who-you-know system?

Savvy applicants for city-owned properties often reach out to their city council member when frustrated at the slow and convoluted process. According to Councilman Daniel Lavelle, who represents the Hill District, council members often walk applicants through the tax sale process, making sure they complete all the necessary steps and follow up with the Real Estate Division to check their application status.

Indeed, all seven successful buyers the Post-Gazette reached said they received help from a council member, community leader or other influential person. One successful applicant, Fritzy Ezzeddine, said the city’s Real Estate Division only reviewed her eligibility as a property buyer when KDKA-TV reporter Marty Griffin called the city on her behalf.

“The fact that a journalist, or a council member or anybody else can come in, and then the property process gets manipulated on behalf of this one-or-other buyer, is a problem,” Mr. Lamb said.

Yet attempting to get in touch with an influential person does not guarantee success.

For months after submitting his application, Mr. Cherry repeatedly reached out to the city’s Real Estate Division and his councilman, Mr. Lavelle, to ask about its status. Despite numerous texts, calls and emails, Mr. Cherry never heard back from them.

“I am aware of his interest and have been in conversation with him,” Mr. Lavelle wrote in an emailed response to questions.