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I don''t pretend to have any answers to the questions of life, but perhaps getting away from Idaho to a coastal place like California, Florida etc etc, and incorporating your regular life, with some coastal cruising, would be a compromise. You can still have jobs, go to movies, and test out cruising to see if the boy will like it. I have a teenage boy who has been on sailboats since diapers. Some months he loves it, some he hates it and wants baseball and playstation etc.
Just a thought