nabla: this could even evolve into a system where people could contribute for one prize (so, instead of having someone pay for a maharajh prize in a tournament, you could have 10 different people pay for 1/10 of that prize).
But a simple automation on the current system would go a long way. The other day someone asked me how to provide the prize for a tournament. After my reply (send money to Fencer saying it's for tournament X) I got a reply that went like "Oh, thank you. Never mind then". I got the impression that, since it wasn't automatic, she just didn't want to go through with it anymore (which doesn't make much sense, since Fencer is the one having to do most of the manual work anyway).

joshi tm: Well, just have Fencer add some support for some cheesy prizes then