Well, I'm not an attending, but I will throw in that the timing should probably be as early as possible (vs. late in th interview season). Calls/connections are good to develop early, and you'd hardly be surprised that these wind up as notes in the applicant's file.
And, *some* institutions have their rank-order finalization meeting soon after they finish interviewing (ours has already occurred), so second-looks or calls late in the interview season don't do much good if you're already buried deep down the final list.
I suppose the solution could be to call/ask the programs when they have their ROL meeting, but the best bet would be to be aggressive early.