The mid-October, November, and first 2 weeks of December are the hot months to interview for FM residency spots. January is too, but chances are you'll be burned out at that point. Doing well on an externship and having a fun time with the residents helps with getting into a program you like. It also exposes some of the weak spots of a program that you might not have picked up on the interview. The ideal situation would be to do an externship, kick butt, enjoy it, interview at that program on the last week, and leave on a real good note. My opinion is that if you really think you might want to go to a certain program, save it for October with maybe 1, 2 at most, interviews during that externship to get some practice. November would be an ok month to do the externship-interview thing, but you risk scheduling a lot of your interviews during that month anyways which would piss off your extern coordinator and residents. The alternative is to do it early in August/September like you're doing when you're fresh off 3rd year clerkships or Step 2's. The disadvantage is that people may forget who you are and have moved on, but it's only a small disadvantage. My advice for FM residency spots is to do them early fast and furious. Everyone just gets burned out when December rolls around and the energy level on both sides is hard to maintain.