Brandon Thurkettle one isn't banned for 5 years until they've overstayed 3 years if not caught by police, and leave voluntarily. 1 day to 1 year o/s if caught by police gets a 5 year reentry ban.
Wise works great. It has an auto conversion tab that let's you select the rate you'd like to exchange at, if you have time to wait for the Baht to move down. Do a Wise-ACH bank link with your home bank and make sure you have enough on deposit in your Wise account to cover the exchange. I made a nice profit on my first auto conversion after the last Baht slide bounced back to the average rate.
The health insurance requirements were dropped to the best of my knowledge, but probably a good idea. If you apply for your visa in the US your bank statements and income source, Social Security, pensions, etc...will be accepted at face value. Here in Thailand there's an authentication process. I don't think the US embassy here "seals" or certifies income statements any longer. Get a 90 day Type O non resident then after 90 days get the 1 year extension