Here's what I got so far-
6 contests from December-May just to start a decent season. You have the whole month to do a contest. First week of the next month, a new contest starts and voting for previous contest begins. If anyone has a contest idea they want to run, etc. pick a month and run it or something. Not every contest has to have a prize, considering I'll be giving a prize to whoever scores the most points over the 6+(?) contests. I'll start one off for December in a bit, thread might actually show up on the 1st since I have a bazillion things to do this evening.
edit: Months might be off, not sure when to start this yet.