Many thanks for the thoughtful and supportive responses above, especially to WGWarburton for taking time to outline all that good advice. I sincerely appreciate it. Champlain Sailor, the book recommendation looks spot on.
We are located in Thailand in a place with remarkably supportive weather and water, which makes things easier. Litigation risk is low here, though being set up in a school environment means both basic ethics and common sense suggest similar safety and insurance practices as you'd expect to see in the West.
The program would be built on the back of an outdoors/adventure curriculum, but would hopefully develop into a competitive athletics activity competing locally and regionally. There are a lot of sailing parents in the school and there is strong support from the administration, but we are starting from square one.
I'm keen to hear any advice as to how to motivate parents be accountable for their family's participation and support. I worry that if the program is considered merely an amenity provided by the school, then parents may not adopt the program, reliably turn up, pitch in, write the occasional check in support, and so on. I'm focusing on this aspect because I believe that if enough parents and students regularly turn up enthusiastically to participate, then the school will put its time and resources into ensuring its a success.
Thanks in advance for your experience and ideas!