Four smiley-face emojis summed up Jessica Gray’s feelings best.

In November, after nearly a year of living in temporary housing, she learned that a brand-new studio apartment in Coney Island she wanted to rent with her city-issued housing voucher had cleared inspection, which meant she would soon have a place to call home.

Gray grew up on Somers Street in the Ocean-Hill Brownsville section of Brooklyn in the 1980s and 1990s in a three-story house her mother owned, she said. Her mom had a vegetable garden in the backyard and liked to cook, so all five Gray children often had the neighborhood kids over.

“Everybody knew each other. Everybody got along. It was like a family-type thing,” Gray said.

At age 40, she now works part time as a school crossing guard in Bedford-Stuyvesant and lives in a women’s shelter in the Bronx. Her path to homelessness was a slow progression of events that began with the death of her mother and culminated in the loss of a second part-time job as a home health aide.

In November, her would-be landlord had given her a December move-in date. Excited about the new apartment, which was much closer to work, Gray sent a text message to the housing advocate, Suzanne Adler, who helped her with her application.

“I am happy can’t wait,” Gray wrote along with the emojis.

“Yay!!!!” Adler responded.

Three months later, she’s still sleeping in a dormitory-style room at the shelter she shares with five other women.

Like Gray, more than 45,000 New Yorkers currently reside in one of the city’s main shelters. Homelessness has vexed the city for decades — rising to roughly 60,000 in 2016 under then-Mayor Bill de Blasio — driven, at least in part, by gentrification and a lack of affordability. At Gray’s annual salary of about $16,000, the neighborhood that raised her is now too expensive.

One of the city’s solutions for solving the homeless crisis is a voucher system known as CityFHEPS — which stands for Family Homelessness and Eviction Prevention Supplement — that helps families and individuals like Gray pay rent to private landlords. Last year, over de Blasio’s objection, the New York City Council voted to increase the housing allowance from a maximum of $1,265 to $1,945 for a single adult seeking a one-bedroom apartment, and from $1,580 to $2,217 for a family of three or four looking for a two-bedroom apartment.

Gray qualified for the program in September last year and counted herself lucky to have found a landlord who was willing to accept her housing voucher. Recipients often face discrimination from building owners when looking for a place, according to voucher holders and housing advocates. But all parties agree that major flaws in CityFHEPS are keeping people stuck in shelters longer than necessary, including an onerous application process that’s easily derailed by even minor errors made by city agencies and homeless service organizations, often prone to simple mistakes.

The chief architect of the City Council’s recent expansion of the program, former Brooklyn Councilmember Stephen Levin, said he’s disappointed in how it’s being implemented. The City Council’s new speaker, Adrienne Adams, said the hurdles recipients face while trying to use housing vouchers are troubling and her office has reached out to the mayor’s office to address the issue.

For Gray, the voucher system’s flaws became apparent on November 7th, when someone misspelled her prospective landlord’s name on her application, causing the Department of Social Services (DSS), which administers the program, to reject her application.

“This needs to be corrected and resubmitted,” John Macropoulos, a partner at Ridgewood Holding Group LLC, the company that owns the apartment in Coney Island, wrote in an email Gothamist obtained —  part of an exchange between Macropoulos and Gray’s case manager at the shelter, along with others involved in securing her permanent housing.

The error delayed the process but didn’t end it. While that mistake was being fixed, another snafu turned up, this time over the walk-through inspection that DSS requires before tenants can move into an apartment.

“There was some confusion that an inspection had failed but that was never the case,” Macropoulos wrote on November 15th. The email exchange does not explain the source of the confusion, but he wrote to the case manager saying an inspection had actually not been scheduled.

Heather Huff of Bohemia Realty Group, a Manhattan-based firm that also works with clients using government housing voucher programs, including CityFHEPS, said what she called “silly” mistakes are often upending applications, even after recipients spend months looking for apartments. Huff said a third of her clients who rely on rental assistance programs see their deals fall apart.

“The landlord loses out on the money, but more importantly these people thought that they were going to have permanent housing in an apartment that they chose, now they don’t have it,” Huff said. “And they're back in the shelter.”

Hoping to finalize arrangements and land on a move-in date for the apartment in Coney Island, Gray said she checked in often with her housing advocate, but she had very little control over the process because the system relies largely on the work of others, including case managers employed by the shelter where Gray was living.

“She kept telling me, 'Oh, don’t worry. Just wait. Have patience,'” Gray recalled.

But patience was difficult to come by. For the past 14 months, Gray said she's longed to leave the shelter in the Bronx, where she has no privacy and can’t get a good night’s sleep.

“I got a roommate in here, she just makes all types of noises at night time doing crazy stuff,” Gray said, adding that the woman empties out her locker and watches YouTube every night with the volume cranked to the max, refusing to use her headset despite being asked to do so repeatedly.

The room at a housing shelter in the Bronx that Jessica Gray shares with five other women.

The room at a housing shelter in the Bronx that Jessica Gray shares with five other women.

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The room at a housing shelter in the Bronx that Jessica Gray shares with five other women.
Jessica Gray

The shelter is also a long haul to her corner in Bedford-Stuyvesant where she shepherds school children across the street, starting at 7 a.m. To get there on time Gray leaves no later than 5 a.m. in order to take a bus and three trains. Moving to Coney Island would cut her commuting time in half.

In December, Gray learned that the case manager who had helped her was no longer working at the shelter and passed her application packet to a supervisor. Gray said she had contracted COVID-19 at the time and was sent to quarantine in a hotel for a week to limit exposure to others living in the shelter. She said she contacted the supervisor for updates several times but most of the time no one responded.

“I emailed him,” Gray said. “I told him please submit my application. I don’t want to lose this apartment because the landlord, they’re not going to hold the apartment for so long.”

Huff, who also teaches real estate brokers how to navigate different government housing voucher programs, said this is not an uncommon occurrence.

“I've had caseworkers that just quit, and nobody knew about it. And, we kept calling and nothing. We emailed and nothing,” Huff said. “That original caseworker had never even passed it on.”

What happened next in Gray’s case is unclear. Black Veterans for Social Justice, the non-profit that runs the shelter where she lives, did not respond to calls or emails seeking comment on why her application wasn’t processed. What is certain is that Macropoulos, her prospective landlord, waited three months for the city to process Gray’s application before cutting his losses and renting the unit to someone else. Gray’s search for a new home started over in January.

“And I can't blame him. I can't get mad at him,” Gray said. “I was crying though because my heart was set on that apartment."

Former Councilmember Levin, who pushed for years to make the program more widely available to homeless New Yorkers, said he previously heard complaints about the process, including from landlords who said they were not paid on time and clients who said their applications were dropped.

“It was not done in a way that was streamlined or efficient or effective,” Levin said.

At the time, he said he couldn’t even get city department officials to provide clear data to the Council regarding how many people were using the housing vouchers. He said it took a few years of repeated requests and hearings to learn that enrollment in the program was dismally low.

“It’s immensely frustrating,” Levin said.

Shirley Limongi, a spokeswoman for Speaker Adams, said the head of the City Council is committed to helping New Yorkers break the cycle of homelessness and get them into permanent housing.

“The hurdles that many recipients are facing in actually utilizing these vouchers is alarming and something we take very seriously,” Limongi wrote in an email. “We are in touch with the administration to address these issues."