Looking at the MAp you posted, and the other info. in your 2nd post.
The only way to do this (And get a good/Reliable connection) is to trench
in some fiber for the over 300ft runs and Cat5e for anything less.
Make it a summercamp project, get the kids to help dig the trenchs/run cable
all the while Educating them in the art of networking..
Not to mention the "free labor" factor
But won't they don't know won't hurt them.