So... my wife has already given me the tentative greenlight to go to the 2014 American Chesterton Society conference in Mundelein. I remember a few years ago on programmers.SE Anna Lear got herself sent to a pretty nice software conference.
I'm not sure if SE inc is still doing anything like that, but if there ever was a conference that appealed (or at least should appeal) to a majority of users of this website, its this conference.
I tried in vain to start a Chesterton/Belloc/Distributism themed StackExchange site a few years ago I got quite a few people to sign up by spamming the leaders of local Chesterton conferences, but no traction from within the actual StackExchange land (there was no C.SE at the time).
Chesterton and Belloc always tied the arguments in their writings back to Christianity and I think that most everything they wrote about could be asked about here.
A contest to build up the number of g-k-chesterton questions would be a natural forerunner to sending the right man (or woman?) to the conference next year (the person with the highest score in the tag in the space of the contest would be the winner. Then, the person who goes to the conference would be expected to schmooze and show everyone the website.