Answers
What does the organizer actually have to do each week?
Less than an organizer expects, if the deadlines are automatic. Challenges are sent by players. Scores are entered by players and confirmed by players. A missed response resolves itself as a walkover. What is left is the part software cannot do: recruiting, answering a question about a rule, and occasionally deciding a disputed score. Budget an hour in the first week and a few minutes a week after that.