if you are 50+, you can apply for retirement visa and then buy multiple re entry permit. With this multiple re entry permit you can go in and out of Thailand any number of time during 1 year of you retirement visa.. If you need further info you can ask me via inbox
Non O can be applied in Thailand on your 60 days visa exemption and insurance is NOT tied up. Non OA in your country required lots of paper works. Sent you the details in your inbox. Hope these info will help you