Ken Chao. Not all embassies/consulates sell the non-O (50+). Australia is one such exception. In regards to insurance, you can use your home country insurance to obtain the OA
Kevin Gustafson. Ok, yeah that would make sense. The only way you're really going to do it is to leave without a reentry permit, and to start the cycle again when re-entering
Keep in mind there's no such thing as a "retirement" visa. There is visa based on being over 50 years of age. You do not have to be retired to obtain this visa, although there is financial criteria to meet
Keep in mind the covid extension is NOT a visa. It's a concessional extension designed to tide you over until you are able to leave. As Benjamin has said, once you leave, its purpose is served