I was intrigued by your question, and the answers so far, since I'll be confronting a similar problem, as a single 40-something woman traveling alone. I have a list of about twenty places I'd like to have a "long term stay" and another thirty or so that I'd like to visit. I plan to spend 2-3 months every year post fire travelling, and would like to explore one of my long term stay options and one or two of the places I'd like to see. For areas I am fairly certain of my safety in and can probably get by in language, I will likely manage with a guidebook, and local guides as needed - Barcelona, Buenos Aires, Paris, etc. For areas I've never been to or don't know much about and will have language difficulties, I plan to do group tours to get a better feel for the place before committing to a long term stay (Japan, Eastern Europe). So likely one extened stay, and two group tours every year.