I like this idea but I think getting fifty participants might be a little bit ambitious. However to start the dialogue, I have a couple of things:

1. What are we going to do with the art? Will it be sent to you and then you post one a day?

2. Rather than pairing a writing type with an art type, since everyone is a writer here, why not have people submit simple prompts for others to pick from? E.g. a scary pup in a Santa hat, someone eating too many candy canes.

3. How much warning will we get to produce the picture?

I would be happy to draw one picture but cannot commit to more than one due to time pressures.