Another idea (although I don't have a specific solution to share) is if someone can create the calendar online through a company like Shutterfly etc. then share a link so that people can order it directly. This would keep the "designer" from stuffing envelopes, taking money, etc. Again, I'm not sure which company might have that option, but I know the BuellXB.com shirts and I believe Dean's shirts are ordered like that. I'm guessing you could do the same with a calendar?
Reading on Shutterfly, you can share a project with friends but the owner has to provide those emails. This could be a fallback plan.
Again...Just a suggestion to make this happen with as little pain to those involved.