Please don't be put off by any perceived negativity you might be feeling. Everyone is trying to be helpful in their own way; even if that means admonishing you of the risks that you are probably already well aware of.
I have volunteered for a teen sailing program for several years so I know something about running a sailing program on a shoe string budget (Sunfish sailboats only). While it would be nice to have a fleet of trailer-able Nor'Sea 27' sailboats (
http://sailboatdata.com/viewrecord.asp?class_id=437) or Pacific Seacraft 25's (
http://sailboatdata.com/viewrecord.asp?class_id=298) to use, that is not going to happen because they are expensive.
I think you may have to start soliciting donations for boats in your local area and decide which ones might fit your criteria. It would be nice if the donors could write off their donations, which I think your organization can do.
The Pearson Ensign 22' I mentioned appears to be a popular boat on the right coast but not so much on the left coast, so boat brand availability varies a bit by location.
Not much in the way of 'cheap' boats on Seattle craigslist right now. I looked. I did find this Cheoy-Lee 31' for what seemed like a modest asking price:
http://seattle.craigslist.org/see/boa/2965091683.html
You would miss your beautiful Formosa 41' but this boat could be a smaller (less expensive) big boat for your program to use for overnights and off shore, if it is in good shape. Use any savings towards a fleet of smaller boats for teaching, racing...
Just throwing out ideas here...
I wish you the best of luck with your sailing program. I'd volunteer if I was in Seattle.
Please do not be discouraged.