Nicely articulated, C-dad. About 2 years ago, a professional sailor was washed overboard and drowned during a gale. He was crewing for a skipper who we know well (Dan especially) and has enormous skills. So this *wasn't* about incompetence. We spent a lot of time thinking about risks, after that.
We concluded that what distinguishes an unnecessary, foolish risk, from an acceptable "the price of doing business" risk is the potential benefit you're seeking when you incur the risk. And that each of us must decide for ourselves what that equation is - how much you value the experiences of living aboard and cruising, and, based on your skill level and cruising grounds, how much of a risk your circumstances represent and how much you are willing to take.
We're with you - having decided that in our case, the possibility of disaster aboard is less than the *certainty* that if we gave up the dream, our sense of diminishement would be its own disaster on land.