After he moved to New York in 2001, Darrell E. Roberson bounced around the Bronx and Harlem, often sharing an apartment with roommates. “People were moving in and out of town, or people had life happening, and that caused me to shift my plans,” he said.

Eventually he moved out to New Jersey and found himself living in Teachers Village, in downtown Newark — a new development primarily for educators — paying $1,420 a month for a one-bedroom. From there, he commuted to the South Bronx, where he works as a middle-school special-education teacher.

It wasn’t until he first made the 90-minute trip that he realized how burdensome it was going to be. With a walk to Newark Penn Station, a ride on either New Jersey Transit or the PATH train, and a switch to the subway in Manhattan, “the commute was really killing me,” said Mr. Roberson, who is originally from Oakland, Calif. “You are on pins and needles: Am I going to get to work on time? Coming home could be even longer. I started thinking, ‘Is this really worth it for me?’”