You asked about ladders, but I played a successful singles round robin so I will describe that.
The organizer set up a schedule giving each pair one week to schedule their match. It was up to them to find a mutually convenient time during that week. Players were warned to work hard to stay on schedule to get in all of their matches. There was a flat fee to participate, with no refunds for unplayed matches.
Once the round robin phase was completed, the players were divided into top half and bottom half. Players did a mini- round robin to determine the winner of the top half. The bottom half players also played a mini-round robin as a consolation bracket.
Most of the bottom half players blew off their matches. The reason was that the whole ordeal was just too long. The round robin had 15 players, IIRC, which meant you did 14 singles matches plus mini-round robin. It conflicted with the start of the USTA spring season, so that explains the dwindling interest.
-- Random Error Generator, Version 4.0
-- Master Moonballer