I'm probably jumping the gun here, as I've never been on a sailboat. But I can tell that there is a good chance I'm going to fall in love with it. Our week-long lessons start in less than 1 month, and we're excited. Wifey has done sailing trips before, but not me.
I see us moving aboard in 15 to 20 years (at retirement). I plan on sailing as much as possible until then. My expectations are that we'll do it until we don't want to, then move on. We may like it so much we don't return, but there is two of us, so we'll decide together.
We're too far away to plan it out right now, but it is on our list. We're constantly simplifying our life. So as it gets closer, we'll ease in to it.