Great questions. I had the bug at a young age and we took a year off from work, rented the house. We left the door open to continue longer, if we found that was our desire.
Toward the end of the year, we were both ready to 'get off'. We loved the experience. In hindsight, we were both changed - for the better - by our year away on the boat. That change was more of a renewed vigor for life, on land and on the sea. At the end, we hit the ground running.
I think we both discovered how much we loved sailing, especially along coasts, for the travel aspect(travel we have a passion for) and natural beauty and quality of life it is.
And so we continued sailing - seasonally - even after going back to work, home. Now, we went farther from home, began leaving the boat in different parts along the east coast. Eventually, we sailed into the area we now live(then with 2 babies aboard).
Where we are(today) geographically and mentally(happily so), may be partly a continuation of that year off sailing.
Here's what I discovered I wasn't crazy about: Making a boat a semi permanent home. It's just me, but the process of making a sailboat into a home takes away some of the essence of what makes a sailboat
a traveling, moveable feast(Hemmingway?).
Coastal sailing gives me all the good parts of that year off. We sail more of our miles now with less stringent schedules. Getting on the boat for a few weeks or days is a lighter experience. We're underway fast, our boats simple amenities(small berths, tiny galley, head, cockpit), give us a real break from our 'home' on shore(and the stresses of everyday life).
Sailing is a way of life for us which we've continued(as a family) year after year. It's not all of life (for us) but looking back and with grown children, sailing was and is a very big part of our lives. We hope to do longer seasonal sails in the future.