I’ve been using Wise and at least for the past year, transfers are always marked as “international transfer”. That’s with Bangkok Bank. Other banks may be different.
in the USA, a single member LLC is considered to be the same as a sole proprietor for tax purposes. So yes, you can do whatever you want with the money.
There is no such thing as a retirement visa. You probably mean a retirement extension on a Non-O visa. A multiple re-entry permit can be applied for at any time.