Thinking outloud re: pick 'em
I'm willing to do it in 2019, but I might cap the number at 40 or 45. For the two years I've run it, usually we start out with 50 or 60 and gradually people forget, lose interest, or give up, and it always ends up with about 15 at the end. So I don't think it's going to make a huge difference. On the other hand, it's sort of cool to get a lot of people to sign up. It's the workload that sucks.
I would simply post week 1 in late August, then it's first come, first served. I sort of slacked on the shenanigans like jokes and near nudes last year. I'll try and pick to improve this year.