Instead of trying to find a career that pays just enough to allow you to get by while sailing, why not get a career you love so much that sometimes you would rather work than sail. Then you have the best of both worlds.
Why not get a career you love so much that sometimes you would rather work than sail?
That is what I did when I became an architect. There are many days when I am deep into designing a project that I think to myself, I can't believe that someone actually pays me to have this much fun. Then there are the other days, but those are why I own a sailboat.