There is the 10 year pensioner LTR visa that is a multiple entry visa. You have to be over 50. It costs 50,000 baht for 10 years. It requires insurance and a passive income of $80,000/year.
My original agent is no longer there. I originally just contacted PC directly. I have a name of someone who handles my renewal but I’ve never talked to her directly. Best to contact them directly or through a broker. Sorry 😞
I bought Thai insurance, Pacific Cross, when I was 62. If you buy health insurance late in life the prices will be higher and there will be exclusions of existing conditions. I bought a 10 million baht policy with a 40,000 baht deductible. Essentially, I am self insuring for the everyday stuff and I have insurance in case something truly terrible (short of death) happens. A large deductible will lower the cost. Also, be aware that many insurance policies will not cover you well in the US so you may have to buy travel insurance if you return to the US for a visit. The OA visa requires insurance. I recommend not getting an OA but pursuing an O visa that doesn't have the insurance requirement tied to the visa and extensions.
If you are over 50 years old you might want to consider the 10 year pensioner LTR visa offered by the Thailand Board of Investment. It costs 50,000 baht for 10 years but you must have a passive income of $80,000/year. It also has a health insurance requirement. There is no 90 day reporting requirement and there are no banking requirements.