Interesting thread. I don't think I can live long term in the Thailand for the reasons that have been mentioned, mainly the cost of health insurance and hassles with immigration. Plus licence checks in Chiang Mai have become a much more frequent part of life than was the case 10 years ago, as has the necessity to fill out a TM30 each time I arrive here -- these are minor irritants, but they can add up. Apart from that, I normally stay in Chiang Mai and hot season there is something I want to avoid, so I really don't want to be resident all year. For me the easiest, least hassle solution (so far) is to come in on the visa waiver program, and leave the country after 30 days for a week or so in Japan and then come back. So far, that's worked -- last year I stayed in Thailand for a total of four months. If I do get push back from Immigration about the visa waiver entries, I'll settle for some other kind of visa. Travel insurance covers me for accidents/emergencies while I'm in Thailand, and if I need treatment for chronic illnesses, that's easy enough to get back home -- it's only a non-stop eight or nine hour plane ride from Bangkok. Thanks to the original poster for being so civil in dealing with the replies. Keeping any craziness and rudeness out of threads of this kind makes them a better resource for everyone.