As I read it, you've got the girl and the dream, and you are trying to figure out how to keep them both (together with you).
My advice is to start VERY early (25 years is not too soon) and take VERY small steps. Visit the same favorite anchorage over and over, until maybe she asks for something new. The most important thing is that she needs to feel that your collective skills (yours and hers) are up to the demands the situation is placing on (the two of) you, or might place on you. Not to use a blunt instrument: she needs to have absolute trust in you in the sailing environment.
The more you can do to make her feel in control and competent, the better. When she's comfortable single-handing your boat, go get your ticket punched, because you've got it made.
Now and then you will screw up. I have, and do, and more often than my self-image has room to accept. If she can't give you absolute trust, etc., even with those events in your history, then the situation can't be saved, and that's a no-fault statement. When I screw up (most recently running aground on a rock ledge in the Perlas Islands on the Pacific coast of Panama) my wife gets very quiet, until I explain the tactical situation, and she understands what the options are, what the tradeoffs are, why I'm doing what I'm doing, and what I need from her (keeping her busy keeps her quiet) and what to expect.
Outside the portholes just now, it's pissing down rain here in Guatemala, with one Pacific low, one Atlantic tropical storm (Ida), and the tail end of a north Atlantic low all within a few hundred miles of us. We've come 10,000 miles since we left San Francisco 5 years ago. We're still speaking to each other.
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