Man, I still don't get that 4chan rally. Who cares about a second-tier Duck Tales character? I was alive when the show was on and I barely remember who he was. How did anyone under 23 or so support it?
What Bacon should do is just set up a schedule of contests in a five year cycle that can be repeated. If he has time to have little side contests, fine but otherwise don't worry about switching things up.
Year 1: Characters
Year 2: Non-VG Characters
Year 3: Games
Year 4: Characters:
Year 5: Something different/GOTD when applicable
There, done. Would this be difficult to stick with?
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"What's wrong with bootblacking? We like it very much!"
This is Yesmar.