In New York, almost every living situation involves a trade-off of some kind. As Joseph Boudin discovered during his first few years in the city, figuring out how to balance the pros and cons of various locations, rents, roommates and apartments is a difficult art to master.

Since moving from Alabama four years ago, Mr. Boudin, 25, has lived in five apartments, each a brief attempt to find a long-term home. After a year in Manhattan, he moved to Staten Island to save on rent, although he was working in Midtown East. When he discovered the commute was miserable, he overcorrected by moving into a Hell’s Kitchen room-share where his rent, at $1,875, rivaled that of a studio apartment. And he still had to travel across town to work.

Then he found a $1,200-a-month bedroom in an Upper East Side walk-up that turned out to be his worst calculation of all. Going in, he knew the accommodations wouldn’t be deluxe. The two-bedroom apartment was small, shabby and on the sixth floor.

“When my best friend moved me in, she said, ‘Joseph, are you sure you want to live here?’” Mr. Boudin recalled. “There was a hole around the bathroom pipe that was the size of a dinner plate.”