There's four different types of documents that are called a "retirement visa". Tod Daniels wrote an excellent post about it.
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> How long does it take?
It depends on which "visa" you're getting. For visa applications you're submitting in person, the turnaround day is usually 1 or 2 business days.
>How much does it cost?
A one year extension of stay is 1,900 THB. A single entry visa is 2,000THB
>Do I need health insurance?
Only for the Non-OA visas.
> if so how much roughly for a 60 year old
We don't know because each person has different health, and requirements. But there is a list of approved insurance companies at
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If you decide to get a "retirement visa" that does not require health insurance, I recommend getting health insurance anyway, hospitals are not free in Thailand.