The Guild lost a large contingent of off-topic participants, so I reckon that'll be the biggest hurdle -- you're working with a much smaller pond.

However, if things get running, I'd like to talk about what I can do to provide first-class support for contests in the software. From storing contests (and their winners) in the database to creating some sort of "Trophy Case" on the user profile. The kind of first-class support we have for Roleplays (in that they have "IC", "OOC", and "Characters" tabs). Making the contest system more visible might encourage participation or at least make it more fun. :)

Reach out if you need help.