I would like to see something like this: Some categories are established: eg: best city map, best regional fantasy map, best space map et cetera. We could even have categories like best original idea, best improved skill member or stick only to more traditional categories like the first I meentioned.
Each year. starting, say, in November, everybody can post a map made in that year; it can be an already published map, even a map that’s already been uploaded for a challenge and that’s been awarded with a compass; or an original one, created specifically for those who would become the annual (yearly) awards (or whatever name you want to give: a sort of academy awards of the Guild; the Guild Awards).
Only requirements: the map should be complete and created in the year of the competition. So everybody would have complete freedom to decide whether to start an opus magnus the first months of the year, or to post something already created for a monthly challenge or for whatever other reason; so, even newbies signing in december could join, and maybe some people that have long term, permanently unfinished projects, could be encouraged to finish their work to join the competition.