Maybe you know a person here with a Thai bank account. You can transfer money when you need to. I use Wize, and most of the time the transfer takes 7 seconds. Sometimes a day, but it would save you money.
I arrived at Suvarnabhumi yesterday. I gave my passport and METV to the IO. She said "I can see that you come in and out of the country all the time". I said yes, that is why I have a visa. It must have been the first day at work because she had to call a superior. I am glad I did not come expecting visa excemption!
I seriously doubt that your insurance covers if you travel all year. I also had a yearly travel insurance, but it does not cover more than 1 month per trip. It is not meant for long time stay.
I do not want to buy health insurance, as the one I bought the first time, was absolutely useless I found out. The insurance company would not cover an incident as they should.
The travel insurance is much better. They do not ask for prior conditions. It covers home transport if needed. They cover theft on top of that. And lastly - it costs baht 15.000 for 6 months.
I just realised that they will see my stamp from from the O-A, which is valid for a few days after I arrive!