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.
At the airport, the airline did ask me for an onward ticket out of Thailand before flying to Thailand. I had an onward ticket for 4 months in the future. They just wanted to see a ticket, the date was not important at all.
Yes, you can do it all just the way you want. Just don’t get the cheap insurance. Get the most expensive insurance (cheap for you and I). My cool pickup truck is in my wife’s name. I’m not worried about that. Married 35 years.