Every instance I've seen of people completing It Takes a Village..Out it has been stated that it required multiple playthroughs, and it was no different for me. I recorded three successful runs of that mission, obliterating everything in site. On the third attempt, I eliminated all but two or three buildings prior to the objective building and it popped.
It Takes A Village...Out is a cumulative achievement.
As of 4/28/14 my Borderlands 2 trading post is officially closed. I am no longer boosting, trading, farming, etc on the Xbox360. I am entirely on the Xbox One now. If you want to play Xbox One with me, send a friend request with a message
to GT zI Drucifer Iz (those are capital I's).