Spot, is this ladder for men or women? I'm just curious.
I have never done a proper ladder. There is a round robin singles thing run by one of the clubs, and I participated one year.
It was limited to the first 16 people who signed up. The organizer then published a schedule. The schedule designated who each player was supposed to play each week (A v. B, C v. D and so forth). It was up to the players to email each other, set up a time to play, and report their results to the front desk after the match.
If players could not find a mutually convenient time to play during their week, they would try to find time during another week. Players with poor availability would often become so backed up that they couldn't squeeze in all their matches. If one player was dragging her feet (as evidenced by the email exchange), the coordinator could award the win to the other player. Not sure if this ever happened.
After everyone had played once, the top half played each other again, and the bottom half played each other. An overall winner was declared at the end.
There were a lot of benefits to doing it this way. Players were motivated to stay on schedule because there was a schedule. Everyone had to pay to play (indoor court time in winter), which was another incentive to sign up only if you really planned to play.
The other nice thing about this format is that you start small (just 16 players), so it is easy to administer. You avoid having some massive new ladder that swallows you whole.
It might make sense, Spot, to have a fee of some sort so that people have some skin in the game and don't blow off all of their matches.
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-- Master Moonballer