Sounds like every fantastic stage suited your life, well done!!
I don’t recommend this 30’er gambit casually. It’s for a young man (as defined) who really wants a change, wants adventure, wants mobility, and isn’t afraid to get sweaty and dirty for a few months.
For him, it’s an amazing chance. If I get a few emails in coming years from new sailors, I’ll be gratified. And your description of your boating life also fills me with happiness at the idea of your joy.
I’ve spent most of my life daysailing and racing sailboats—mainly Herreshoff 12s when I was younger, and then Dark Harbor 20s for about 50 years:
http://features.boats.com/boat-content/2004/07/from-a-dark-harbor/
But I’m afraid I’ve gotten a bit too old for racing. In fact, now I mainly go out in a kayak, since it’s good exercise for the arms.
When I was younger, I dreamed of sailing single-handed around the world, but then I got married, had a family, and didn’t really have the opportunity to do it. But we did used to have a good time sailing with myself and various children, and going ashore with sleeping bags on the Maine islands before anyone else thought of it.