Bukkit

What is the enhancement in mind? How should it look and feel?
The idea is similar to the points system: If a player breaks the filter rules, or breaks them too much, they are punished.
My idea for a punishment is to charge them X amount of money. If they don't have enough money, their chat/command/sign action is not permitted, or they are kicked (choice of server setup).
Though there is a way to run a command console side to deduct money, there is no way to check if they have enough money to decide to allow or deny the action.

Please provide any additional information below.

Player likes to say an annoying phrase (swag for an example) a lot. If they refuse to follow the warnings given, they are punished.
If the player does not have enough money for the chat filter, their chat does not go through.

This will be part of a future feature enhancement that allows some "conditional" paths in the rules. It is not trivial, though, so will take some time.