My friend has a OA visa that he extends every year I’m Chiang Mai. Latest time was this year on the 28th of October, so just before the new regulation enters in application. He was not ask for any insurance. He got same time his multi re-entry permit. Then he left Thailand to flight to France on the 14th of November and he just came back today 10th of
December. He flew as usual with China Eastern Airline, so he had to pass immigration in Chiang Mai. He had no problem at all to enter with his OA visa, no insurance. He told me that the officer did not even speak about anything related to that point. So he went through immigration in less than 5 minutes. Of course, next year, for the next yearly extension, the story will be quite different.