Wow, I can see you have put alot of thought into this! Really love your post and all your ideas. The idea of getting out of the rat race is quite appealing to me at the moment, as I have just been out of work for over 6 weeks, skint and suffering, although I have just landed a perm job in Bristol as Web Developer where I live so that is good. I was thinking while I had so much time on my hands that I would just love to have the time to do what I really want to do which is practice my ashtanga yoga and teach, and play my indian music, I sing and play sarod and teach (www.sarodplayer.co.uk
, currently focussing on my yoga though as I don't have time to keep a day job, yoga and music going).
Financially it could work for me as I can monetise my skills and work remotely in Cyprus to a certain extent with the Web work, although I would prefer to just do the yoga and music, it might be possible to teach classes to tourists and perform in local cafes and restaurants etc.
Family wise it could work out for us if we get on as I am 48, bi and dating men and women, she is 58, and has never been interested in any relationship other than with me, we've been together nearly 20 years now, I opened up our relationship for last 3 years and she is okay with that, she would love to get the sun as she is not a well person, suffering with Chrons Disease, hasn't worked for over 20 years, sun would be good for her and she always keeps herself busy around the house, helping friends and old people, gardening, shopping thriftily, we also have a 16 year old daughter.
It is a dream but could become reality, a friend of mine has lived communally, he may have some advice. I also like naturism.