Thailand from October to April. I’m from the US, so my circumstances are similar, but not the same.
I have Medicare Advantage plan in the US and my plan will reimburse me for any emergency hospital visits. I have to pay in Thailand and submit the bill to Medicare when I arrive home. The plan states I cannot travel outside the United States for longer than 6 months each year. For all other medical expenses in Thailand I am self insured because I spend B5,000 or less each year. Works good for me.
Can you get a 60 day visa waiver? Then get a 30 day extension? You can buy most meds in Thailand. No need for buying insurance, be self insured like me.
within 60 days was not relevant in my case. My ticket out of Thailand was for 4 months in the future. The airline staff just wanted to see an onward flight and the date does not matter.