John's office and the diner are overrun with homeless people after a nearby residential-care facility is closed, so John goes to city hall to complain. Also: Jake receives a large check from his late grandma's estate and must decide what to do with the money.

Margaret gets depressed and refuses to work after she learns that a long-time friend is now worth millions. The information leads her to ponder whether she could have made it as a professional singer if she had pursued her dream. Back at the office, John tries to train Linda to give flu shots.