Can you change a visa exempt status to a Non O visa while in Thailand, or should you apply for a 60-day tourist visa first?

@Haydn ******

yes he can if his Thai immigration office allows for obtaining the Non O for retirement and then the one year extension of stay based on retirement.

@Haydn ******

Got my Non-O once in Thailand (2018) : 1. Entry on "ENTRY EXEMPT" (30 days), 2. then applied for "EXTENSION" (30 days). 3. About 20 days before the expiry of this extension, applied for the "Non-O", got it (valid for 3 months), 4. About 3 weeks before expiry of Non-O, applied for "One Year Extension based on Retirement". To extend every year if requirements still met (finance, lease contract, etc.). If you travel outside Thailand, you must ask for a "Reentry Permit" (otherwise you lose your "One Year Extension". Hope this helps. ;-)