Sorry the above reply was short (it's 4:45am and i just woke up).....
I had a deal with the sports organizations that worked pretty good - maybe you or some others could use it. I would contact every schools newspaper/yearbook staff and offer to supply them with a team picture at no charge if they would allow me to offer the pics to the teammates. About a week before the shoot I distributed order sheets so the students could order individual packages if they desired.
When the day came, I always shot each individual player - whether they ordered or not. It was surprising how many orders I sold to families that "forgot" to return their sheet. It is all prepaid.
I used film, not digital. When I sent the film for processing, I simply made a list of what the lab was to print for each frame (using a professional lab is important) depending on the order. When the prints came back my staff simply inserted them into memory mate folders and we delivered them to the school for distribution.
It sounds like a lot of work but not only do you make money on the individual orders - you'll be surprised how many jobs you'll get for senior pics, weddings, etc...... all because you gave the school a 5 x 7 team pic.
I hope this helps...
Bob