I've done some work creating an automated ladder system that currently supports Quakeworld and Quake 2. check it out:

http://subsurface.se

The User-experience is (or in most cases, it is beta)

1. Signup
2. Install plugin (game clients for select games is installed here)
3. Click <Play Ladder> button(s)

When there is an opponent available game client is launched and both players are connected to a game-server that is password protected for the duration of the game.

When the game ends, the ladder-system collects score and updates the ladder ranking.

Server selection
Server is selected from a pool of available servers. The ladder-system uses a trivial algorithm to determine most fair server.
the server with lowest ping1+ping2 + pingdif

When a server is selected, the ladder-system use rcon to setup the server with password, maps and other settings needed for the current ladder.

post on quakeworld.nu