Dave,
Thanks for sharing your thoughts. (Sounds like we started losing our hair at about the same age. I've always opted to look at it as a sign of incredible virility and masculinity.)
As others have said, go for it and don't look back. Mistakes will be made, issues (mechanical, weather, social) will come up and have to be dealt with... that's all part of life and is really not that much different than life on land. If it doesn't work out, you can sell the boat and have a chunk of change for a new dirt dwelling.
My grandmother tried to convince my grandfather to sell the house, buy an RV, and hit the road. He refused. After he passed away, my grandmother said to me, "I wish I had... and now it's too late." Don't be her. Go for it while you can.
And please keep us posted about your search, your learning process and your travels.
John
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