@Vanessa *********
actually, you can arrive with a 60 days tourist visa. You will need to open a Thai bank account, and transfer a minimum of 800,000.- THB onto it from the USA. Then visit Immigration and apply for the "change of visa type" from the tourist visa to a "90-days Non-Imm-O retirement visa". No proof of health insurance needed, it is a "no fuss" application, costs a fee of 2000.- THB. You will be issued the visa firstly, for 14 days "under consideration" and need to pick up the stamp 15 days later. And as soon as the 800,000.- THB have been sitting in your account for 2 months, you can apply for the "1-year extension of stay permit based on retirement". No health insurance required! (however I emphatize one should at least hold a good insurance when abroad) Check the requirements for the "change" carefully and look if this might be an option for you, as the Non-O and the subsequent extension are a much "easier" option for a longstay
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/9.FOR-RETIREMENT-PURPOSES-50-YEARS-OLD-NON-O.pdf