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I think of the tax code and corporate issues as straight forward and an accountant will easily identify these issues for you if you'd like. i think that this is a fine idea and i know, just from the people who buy my book, that your "real" audience may be the dreamer still grappling with these ideas and filling time until they either go for it or decide against. many (maybe most) of my readers still have yet to make the plunge. i can see your audience including many of these same dreamers.
one observation is that a fair number of your subjects may be best taught on the hard or in a slip. learning underway is a fulfilling but includes a large number of challenges/variables that make learning technology and systems difficult.
i crewed an international race once in which more than one team did not know how to heave to or handle heavy weather. we've all seen sailors misuse GPS and I once watched a sailor slam his boat into a buoy that he set as a waypoint. people do pay more than $2k just for a few weekend course in boating/sailing. Just be properly licensed, take strict precautions, buy more insurance than you'll need and I say go for it.
Mark Nicholas
The Essentials of Living Aboard
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