Here in Seattle we work through Sail Sandpoint -- a non-profit organization that has a fleet of Hobie Waves and Hobie 16s, as well as the usual gaggle of 420s and Optis.

We find people willing to donate 16s. In exchange, they get a tax write-off. I wonder if your school entity -- or another non-profit organization (like Sea Scouts, or...) can help provide the donation framework. We are now up to 6 16s -- all donated.

We also got some of the local sailors to make cash charitable contributions, and we will use that $ to upgrade and maintain the boats.

Oh! I almost forgot! The Hobie Waves were also donated. All brand new! We got corporations and boating industry groups and private individuals to buy and donate them. Again, the 503(c) status helped.