@Alex *********
*** you have definitely been misinformed.
Any foreign insurance like the Cigna will only be accepted for the first two years of stay permit you can squeeze out of a Non-Imm-O/A Longstay visa. If you switch to the 1-year extension, Immigration only accepts a tgia-listed insurer.
*** in order to switch from a Non-Imm-O/A Visa to a 90-days Non-Imm-O Retirement Visa, you would need to exit Thailand without a re-entry permit during the “second year”, as this would void the most recent stay permit you got out of the O/A visa.
You cannot apply for a new visa as long you are still on a valid visa or valid stay permit. It needs to be voided before you can apply for a new visa.
This means it cannot be done within the first year, because the Non-Imm-O/A visa comes included with a multi re-entry permit valid for the first year of the visa validity
*** regarding WISE, the solution is setting up a bank account with Kasikorn. The proof by Kasikorn that WISE was involved can theoretically also be applied for if you have any other bank’s account, but if your account is with Kasikorn as well, the procedure of getting the proof from them is the easiest