On a Non O Retirement Visa you are required to apply from your home country in order to extend it. I hired a legal service to do it for me and went home to visit family and it was approved in a few days, but I spent a couple of weeks at home.
There's plenty of work around options for you. Try to work with the airline to route you around the no fly zone. If not, I would demand a refund. Nevertheless, you must leave the country or risk not getting your extension. The choice is yours.
You have to apply for a Non O visa from your home country. But in your situation, you should just use the 60 day tourist visa. When you're ready to come on a more permanent basis, you need to do your research ahead of time and make sure you're doing everything correctly and don't try to cheat the system.
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