I am resurrecting this old thread because I was wondering the same thing as the original poster and found this thread.
On another motorcycle website I frequent, they have a monthly photo contest. The winner of each month is featured on that months calendar page with runner ups smaller on the page.
That website uses
www.cafepress.com for the calendars. The beauty of cafepress is there are no minimum orders or run sizes. There is no cost to design or put them up for sale. Each person who wants one, orders on their own so the website has no cost. A profit margin can be set from zero to whatever if the website wanted to make a few bucks off them. We set ours to zero. Thats the up side. The downside is each calendar is more expensive than the ones where you have a minumim order of 100+ and then the website sells them. But there is zero risk to the website being stuck with calendars they couldn't sell.
What that website does is uses the Nov and Dec winners from previous year so the art can be done by year end. So our 2010 calendar will have Nov and Dec 2008 winners and Jan-Oct 2009 winners.
To see how these work, heres the link to that calendar. I am the MAR, APR, and OCT winner on this one..
http://www.cafepress.com/vcal2010.422617139#Anyway, just something to think about.