It's encouraging to see that there are other like-minded souls out there! Maybe we're not as daft as some of my friends think!
I'll be 51 this year, have only been sailing for two years. Like many of you, we intend to cruise after I retire. Being the "jump-in-with-both-feet" kind of people we are, my wife and I bought our boat before either of us had even taken a sailing course. I don't know if our skill level (or ambition) will be up for an ocean crossing by the time we retire (5-7 years, God willing) or whether we'll stick closer to shore. Either way, I think We'll be as happy as a clams living the cruising life for a few years after I retire. Someday, of course, we'll have to "swallow the anchor" as age catches up with us or the waunderlust fades but, as long as it's fun and our health holds out, I think retiring onto our boat and simply bouncing around from place to place will suit us fine.
I wish all of you the very best of luck as you each chase your dream. May reality rise to your hopes and expectations!