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Not sure where you plan on doing this. There are schools now, some very well established and marketed, that offer live aboard classes to prepare couples for taking off. That is just one of the many classes they offer from entry level to racing.
At the end of the day, after boat expenses and captains salary, you will be lucky to cover half of your boat expenses. True, it is just one boat that you want to book for X part of the year. However, there are efficiencies in numbers which you do not have.
If your boat is beautiful, in a beautiful place, and your captain/instructor is a great person/teacher/cook/story teller/mechanic/sailor you may have a chance. You just have to figure out how to tell the consumer about it.
Good Luck
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