When you are doing residency interviews, what are good strategies to really scope out a program and get a sense of what your life could be like there?

Are you able to talk to Residents already in the programs? I would think that they are the primary info source. Have your chats before your interview, of course.

I think there are two issues. First, decide if you want to spend then next 3–5 years of your life in that city (depending on residency) or more (if you do fellowship there). This is critical. You don’t want to be miserable at work, and at home. Second, try to talk to as many people as possible. Ask them not to sugarcoat their answers. Every program has dirt, and dirty secrets. There are no perfect places, and the people who paint a completely rosy picture are full of shit. Then, try to balance all the good things you know about the place with what you can tolerate of “the bad”.