The best answer to your needs is to stay where you are. SSI most likely will not be enough. Medicare will not pay bills acquired here in Thailand. To get an O visa you need about
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million Baht and Baht 50,000 or more per month income. Insurance will be far more than you can afford if you can get any. I am healthy with no medical problems needing regular care or meds. At 85 insurance is sky high. I have several million Baht set aside for when I need money for emergency or health care. Multiply what money you have to work with by 35 and that will be close to the Baht you will get for that money. // Good luck.