Re: Making a living as a liveaboard
Another option that has not been suggested yet is teaching. Many countries will hire Americans to teach English or perhaps a specific skill that they cannot hire their local teachers to do. Of course, this locks you into a country for a full school year, but you would get the full exposure to the local way of life and learn the culture. Friends of mine taught in Marsh Harbour in the Bahamas for two years. It was a great experience for them and the government gave them a monthly allowance for housing, so if your living aboard, you rake in both the salary and a stipend!
I teach AutoCAD and GIS programs so I could imagine finding something along those lines as well as English.
Tartan 37-C, #59