It would be a great idea
The chip collectors at Chiptalk.net have done the same thing. They mostly deal with playable sets so they would submit photos of full sets in stacks or shots of the chips in play etc. I don't know how many years they have actually been produced but there is often a submission thread in around September or October for new calendar photos. It would be great for a calendar like this if you could put several of the "holy grail" chips and the COTY chips. The hardest part is getting good photos, as the photos themselves will sell calendars to the non collectors. I look forward to seeing a final product