When is the best time to do outreach to programs to express interest in the program?

Your specialty advisors are the best resource for this question because they are the closest connected to how that specialty reviews applications. Generally, if there are specific programs that you have a strong interest in, then definitely consider reaching out to the program. If it's after the second week of November and you do not have the interview requests that you are hoping for, work with your specialty advisor to develop a plan for outreach.