I had great service, an excellent exchange rate, and VERY reasonable cost doing a simple bank-to-bank transfer. It was under $40 total for both bank fees. For $24,000. Took two business days, though they said 3 business days.
Wise is fine for under $1000. Above that it can get stiff.
No sir.......no health insurance required on a Non-O retirement visa. You may be thinking of a Non O/A visa. Very easy to get things confused in the byzantine world of Thai immigration rules, which even then changes in some of it's requirements from immigration office to immigration office. Plus even then a Thai immigration officer has a LOT of flexibility in dealing with any one applicant. I learned that the hard way.
Its a LOT easier to have an injury accident and/or a serious illness here in Thailand than in the States. IMO, definitely get travel insurance. Plus it covers problems with your flights/luggage etc. Well well worth the price!
Do you have a landlord that you trust and has a passkey? Or no GF who has a key? If so, have them send your cards to you via courier. If not, try calling the bank and tell them you are visiting where you are and ya lost your card and ask them to send you a replacement.
Buses to Pattaya run like every hour or hour and a half from the BKK airport. The bus ticket kiosk is at the bottom level down by door 8. The price was something like 160 baht the last time I rode it, if memory serves. It makes a roadside stop at north Pattaya, then it goes to south Pattaya to the Jomtien bus station.
Right there next to the bus ticket kiosk is the entrance to the food court also. MUCH cheaper than the other places to eat at the airport. Buy a card at the entrance, cash out the card when you leave for any change left over.
Keep you wallet in your front pocket in crowds. Maybe use a money belt to keep your bigger cash and credit cards and ID's in. A chained wallet does not help. A pick-pocket just uses that chain to get you wallet out easier. Don't ask me how I know that. Whatever the case, chained wallet or not, keep it in a front pocket and don't keep big money in it nor more than one credit card.
GOOD LUCK!! I say that all seriousness. I would hate to be trying to raise a young man in today's world. God be with you and your wife, and may He protect the young man in this critical and difficult time in his life.