The tale of the lease buyout is almost mythical in New York.

It goes something like this: A tenant with the good fortune of a rent-regulated apartment in a hot neighborhood negotiates a six- or even seven-figure payout in exchange for the keys. On the surface, a buyout may look like a sweetheart deal for a tenant. But tenant advocates say the reality is often dark, with landlords preying on vulnerable tenants and bullying people into leaving their homes for paltry sums.

Even under the darkest circumstances, though, plenty of landlords still cut the checks. But what happens if they don’t?

On Jan. 31 of this year, Machiveni Tigrai moved out of his rent-regulated, $1,720-a-month one-bedroom apartment in the East Village, expecting to receive a $260,000 buyout. He piled his belongings into a U-Haul and handed in the keys. But his landlord did not give him the money. Instead, when he called, he just got voice mail and silence.

So Mr. Tigrai, 37, who works in technology, slept in his U-Haul in the middle of winter, afraid to leave his belongings unattended. As the days wore on, he became increasingly anxious. He did not want to sign a lease on a new apartment until he had the check in hand, and he did not want to pay for storage. So he stayed with the truck, some nights sleeping on friends’ couches. “You’re always kind of anxious with a deal of this magnitude,” he said.