It used to hurt, but my wife told me to stop complaining. Now life is good. We do round trip from near Chicago to BKK. To Thailand in mid-October and return after Songkran. We fly premium plus for about $3000 each. I found premium plus is more comfortable for me than business class.
I believe one last step to what Brandon explained so precisely is that you need to get a re-entry stamp so your visa is not voided upon departing Thailand. I made that mistake.
my Thai wife has a bank account and we can transfer money to the account from the US using MoneyGram. Haven’t needed that for a few years. More importantly, my wife has the bank account app on her phone and uses the scan-to-pay feature. We do that all over Thailand and it is free, no fees. Brilliant. We never use or need ATM or bank debit card.
I was flying from South Korea to Thailand and anticipating getting the visa exemption on arrival. The airline demanded to see the onward flight. My flight from Thailand to the US was for 4 months in the future. The date was no issue as long as I showed the ticket.