Its whatever works best for you. For me it's much easier to send to my thai bank and use scan and pay through my banking app. But I also have a US bank card that refunds all foreign atm fees, so I use that to have cash to carry. You always need backup, so have multiple ways get your money.
Get the non O so no insurance required. You can get travel insurance up to a year. That gives you plenty time to get here and figure out what you want to do about long term insurance.
is he talking about the initial 90 day O or OA or the 90 day and the extension? It's not clear. If he's talking about the extension also and wants to use the