Regarding all there great adages and stories about finances, what I do hear and believe myself is that although most of the time it seems that if one stays locked into their job and a life of financial security: no risk is taken and little is gained.
Good thread, and lots of interesting replies.
What I find is common, however, is that "going cruising full time" is fairly romanticized, while "ocean sailing for four weeks a year" is presented as a poor, weak substitute.
As I read more of the sailing quarterlies here in the UK (from the Cruising Association, from the Westerly group, from the Rival group, and more), you realize that cruising successfully, for four weeks a year, with pre-teen children is a decent and rewarding achievement in itself. It's a life-long touch point for the kids, it changes the nature of your family, and the achievements can be remarkable.
That type of cruising (for example, two weeks to Holland and back) is also something that is achievable by a middle income family, with an older boat, experience and a will to do it. Many of the sailing mags around here are about how to pick up a boat for very little, fix it up, and then go sailing and cruising safely. (An added benefit is not having to quit your job, sell your house, spend your savings, lose your health insurance, etc.)
When I read books by Liza Copeland and others, who did cruise full-time with their kids, even they sent kids home for high school years and the like, because the overall effect of long-term cruising for kids can be a two-edged sword. Not just from a socialization viewpoint, but from the idea of them having summer jobs to save for college.
My two biggest financial concerns regarding cruising full time with kids having nothing to do with my own retirement or returning to work after the cruise. The two real problemis having family health insurance for 2-6 years while cruising, and then having something saved up to help the kids with their college costs when we return. Even state colleges today (and five years from now) could put a kid seriously into debt with college loans.
Anyway, keep things in perspective, and celebrate the cruising you've done and can do even if you keep working. Yes, we could all die tomorrow for one reason or another, but that doesn't take away the cruising we did two weeks ago, or last summer, or for the last five years.