Great idea and a lot easier than it sounds. Just start a list, ask who wants to be in the Calendar then sort out the photoshoots, plenty budding David Bailey's around here who i'm sure would be more than willing to do their bit ! Guess the biggest problem would getting a designer and printer but I could easy help out in that department in some way if need be.
We (Aberdeen Scoobies) have done one for the past 2 years and have shifted over 200 copies between them raising almost 2K, that's just selling them up here, i'd imagine an SIDC one could shift some really good quantities.