As you mention, you've gone back in business. That's a rising trend instead of classic retirement. If you've worked for yourself all or most of your life, we find that pretty easy. But other boomers are taking that challenge and enjoying the energy starting a business can bring to their lives and the money may help with sustaining lifestyles people enjoy. Mostly though, it's usually a healthy option.

Then I'm seeing many people supporting their cruising or extended sailing(what I like to do), with income from renting properties(mostly their homes). In fact that scenario seems to be the foundation for many people I'm connected with this year that are sailing longish term. And I see that as not such a long term event of multi year cruising and living aboard, more an adventure with a beginning and end. There are many adventures out there besides sailing.

From what you have said in your post, these notions seem to reflect what you're doing as well. I'll be interested to hear what sort of transition you make in your sailing life. I think it's a shame when people just stop instead of adapt to their situation.

I especially agree on the boat re-sell. Unless you have something that someone really covets and values(rare), you're going to take a hit, or not sell. I'd gladly give our cherished boat(of little and waning value), to one or both or our kids one day except, depending on many factors, it can be such a liability in the wrong hands.