Not sure what you are trying to say but as land borders are open you can travel to a neighboring country, the closer you are to a land border the more likely you are to be rejected for a unable to travel extension.
Far easier to do it in country than back in your own.
60 day tourist visa, extend by 30 and apply for the Non O based on retirement when you still have more than 15 days left on the 30 day extension. Then the 12 month extension to your Non O Visa.
Gives you time to find a good place to live, sort out all the financial stuff and used to dealing with immigration.