Or you could get insurance between now and then. In any case, there are more recent reports that there has been a change at Immigration at Suvarnabhumi that they are now letting people in with OA before Oct 31 and stamping them in for 1 year. The change seems date from November 7th. Basically, it is all still in flux.

If you apply for an OA in your home country the required document is the same a before + now you need health insurance. Your money can remain in your home country.

If you enter Thailand on non- O the you can apply for a 1 year extension. You do not need insurance but your money has to be in a Thai bank. First you buy the single entry O visa and the the 1 year extension and there are no regular border runs though you still have to 90 day reporting as you do now.

Yes. Wait to see what happens but it wouldn't hurt to explore what the current insurance options are now. If you are on yearly extensions then they are going to probably require a Thai insurance policy. You should look into these now and weigh the implications knowing you have time to wait this out until August next year.

You have four months to look into continuing with a non-O visa and then a 1 year extension of stay.

I would stay away from an OA visa at this time. You already have an O visa and stated an intent to buy health insurance. Follow the process to go directly to a 1 year extension of stay. Buy a good value insurance policy that meets your needs. Don’t get caught up in the current OA insurance confusion.

My landlord registered for the app. If filing a TM30 ever becomes burdensome for her then I will suggest she give me the login and password and i will do it myself. So far she wants to do it and I don't travel very much.

I believe you would be stamped in until the date your insurance coverage ends. If you want to be stamped in for a full year you would have to synchronize your insurance coverage to start near the end of your current visa.

If you are a tourist staying in hotels then the hotels have already filed your TM30s.

A tourist for 1 week? Of course not. It specifically applies to people getting a non-immigrant O-A visa at a Thai consulate in their home country. And as a US citizen you can arrive without a visa and you will be stamped in for 30 days. It doesn't even apply to people who get tourist visas.

You might try to get your insurance company to write their own letter summarizing the inpatient and outpatient coverage and whether they will cover someone living long term in Thailand. No one knows how this whole thing will work. It might be worth a try.