When the man arrived, Mr. Shea smuggled in his luggage in a laundry cart so as not to attract attention from his neighbors or the co-op board of his affordable housing development. He told the man to say he was a friend if anyone asked. But once upstairs, the man suddenly decided to leave, saying that the shabbily decorated terrace that September night was too hot.
The next month, Mr. Shea received notice that he was facing eviction proceedings. The man from Miami, it turned out, was actually a private investigator sent in by his co-op board. Mr. Shea, 78, is now fighting to remain in his apartment, arguing that eviction is an excessive punishment.
“If I get kicked out of here, I might end up homeless, and I’ve been homeless before,” he said last week in the fading afternoon light on his terrace, a sweeping view of Midtown behind him. “Or I’ll have to move to some small town where I know nobody. And believe me, once you hit my age, it’s very, very difficult to make new friends.”
His case — and five other recent eviction proceedings for similar infractions in Penn South, his co-op development — has become another battleground in the fight over whether New Yorkers should be permitted to rent out their spare beds, rooms or entire apartments to travelers through websites like Airbnb.
In September, hosts won a victory when a New York City administrative panel ruled that it was legal to host an Airbnb guest for a short-term stay if a resident was present at the time. Last month, Eric T. Schneiderman, the attorney general, pushed back, subpoenaing Airbnb for the records of some 15,000 hosts, citing the loss of millions in hotel occupancy taxes. Mr. Shea’s case is yet more complicated, because he broke both his co-op’s rules and city regulations governing the terms of his subsidized apartment.
Penn South, where Mr. Shea has lived since 1993, is a kind of Shangri-La for middle-income residents. Spanning nearly five square blocks of mouthwatering real estate between Eighth and Ninth Avenues in Chelsea, its 2,820 co-ops sell to people off decades-long waiting lists for prices set far below market rates. (A three-and-a-half room apartment costs about $ 69,000, for example.) As a senior dependent on social security, Mr. Shea also got a city subsidy for his maintenance charges, so he paid around $ 500 a month for his studio.
While he suspected that the board would not approve of his taking in paying guests, Mr. Shea never asked, mostly because he did not want to know for sure, he said. He estimates that in 2011 and 2012, he hosted about 50 travelers on his terrace, which resembles a cluttered den clinging to the edge of the 19th floor. He earned, he thinks, about $ 6,000.
“I told them at the hearing, you didn’t have to hire a private investigator: If you had asked me I would have admitted it,” he said.
This would not be Mr. Shea’s first brush with hard times. Born to a single mother in 1935, he was kicked out of his home at age 15, in part for being gay, he said. He survived as a teenage prostitute in New York City, he said, until a professor he met in Philadelphia took him in and got him a scholarship to college.
He later became a typographer, working in ad design and computers. He floated in and out of estrangement from his family, and over time came to accept that close relationships were a challenge.
“I’m really at my best around strangers,” he said. “Other people get on my nerves after a while, and I can’t let things slide, so they get on my nerves more and more.”
In fact, the idea of hosting guests started as a suggestion of a therapist, who suggested it might help with his deepening isolation and depression, he said. He started renting the terrace through Airbnb and Roomorama, and was soon hosting guests from New Zealand to Oklahoma, drawing up lists of landmarks and making coffee, for $ 65 a night. “David is a great host, and has extensive knowledge of the area,” wrote one Airbnb reviewer named Patrick from Melbourne, Australia. “Just don’t be a prissy cleanfreak and you’ll be fine 
!”
At Penn South last week, several residents said they believed eviction was too harsh a punishment for a resident who occasionally rented out a spare room or bed. Sari Rubenstein, a woman in her 40s who has lived there most of her life, said her own elderly neighbor had been evicted recently for the same reason.
“I don’t think it is right for them to throw old people onto the street,” she said. “I think it’s cruel.”
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