I know that they require you to be on a non-o visa so you have something to existend.
It seems you can apply for the 90 day visa outside of Thailand.
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That would maybe save you some time.
Again there's actually no retirement visa which people will tell you but instead raise a non-O immigrant 1 year extension for retirement reasons.
I think already the 90 day non-o is (or can be) "for retirement" do what people think of retirement non-o visa is actually just the 1 year extension...