Winners Pot-Pooling Money:
Check with Grim/Hoof, but I think that's not permissible. We used to run contests regularly and as I recall they considered this gambling, so we had to make some adjustments and I don't want to say exactly for fear my memory is off.. I may be not remembering the details correctly, but before you step in a hole, check it out and clarify how you can conduct it.
I may have missed something but I think a Winner's Pot might be permissible. There were no issues when we raised over 1000 fsp (I forget exact amount, 1200-1400 fsp) for the Grand Graphics Tournament last year. That included entry fees from participating artists, donations from the FS community, and funds raised from the GGT auction (all donated art, over 100 pieces. And bids ran high on many).
I see no reason why a pot couldn't be started for the GvG Tournments.
An entry fee of say 10 fsp per participating guild? (more guilds join in, the bigger the pot).
Maybe have a pvp rampage where the loot goes towards the pot? (Obviously a lot of fun for the pvpers, not so much fun for unlucky levelers!)
^ Just an idea. Don't shoot me for sharing!
If a winners pot for the next tournament gets started, I will gladly put in a donation of 100 fsp.