What are the options for obtaining a long-term retirement visa in Thailand for someone over 50?

A good reason to get the O-A Long Stay Visa in your home country ... is that this visa is actually good for more than one year... Each time you Exit and Reenter Thailand in the First Year (using the Multi-Entry aspect of this Visa) - you are Extended automatically another 12 months of stay... When this is done just days before Expiry of the First Year - you are Extended a Full additional year ... The second year is a bit different - you still report to Thai Immigration every 90 days but you cannot Exit and Reenter without a Reentry Permit which you have to purchase at Immigration... Plus at the end of the Second Year - one can then opt to apply for a one year Extension of Stay Based on being age 50 or over... In my opinion it is the best visa anyone over age 50 can get.

This is the have your cake and eat it too visa...

okay, lets sort this out right now ;) despite what everyone under the sun (thai official and foreigners alike) there is NO such thing as a "retirement visa" period end of story.

There is a year-long, multi-entry Non-Immigrant Type O-A (Long Stay) visa that you get in your country BEFORE you come here. which requires you be over 50, a police background check, a medical certificate and meeting the financial requirements

OR

There's a 90 day single entry Non-O visa granted on the basis of being over 50 and meeting the financial requirements. <- This can be gotten inside the country at the immigration office or at a thai consulate before you come here

Once you enter on that you then apply for a year extension of stay based on being over 50. <- that is what is called a retirement visa by most people (immigration officers included) and it's the one that has the word "retirement" stamped into your passport.

Actually that extension has nothing to do with whether you're retired or not, only that you're over 50 and meet the financial requirements. In fact the actual thai wording for that extension is called "in the instance of living out the end of your life" (กรณี ใช้ชีวิตบั้นปลาย):O