What are the steps and timelines for applying for a Non-O visa in Thailand as a retiree?

Why don't you get your Non-O in the US before you travel then start the extrension process during your 90 day stamp?

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𝟭. 𝗪𝗵𝗲𝗻 𝗶𝘀 𝘁𝗵𝗲 𝗹𝗮𝘁𝗲𝘀𝘁 𝘁𝗵𝗮𝘁 𝗜 𝗰𝗮𝗻 𝗮𝗽𝗽𝗹𝘆 𝗳𝗼𝗿 𝘁𝗵𝗲 𝟵𝟬 𝗱𝗮𝘆 𝗡𝗼𝗻-𝗢 ?

That depends on the immigration office you use for the initial 90 day Non-O visa. Most offices require a minimum of 15 days left on your current entry stamp (or the 30 day extension from it) SOME require 21 days remaining, SO check with your office when you get here

𝟮. 𝗢𝗻𝗰𝗲 𝗮𝗽𝗽𝗹𝗶𝗰𝗮𝘁𝗶𝗼𝗻 𝘀𝘂𝗯𝗺𝗶𝘁𝘁𝗲𝗱, 𝗵𝗼𝘄 𝗹𝗼𝗻𝗴 𝗱𝗼𝗲𝘀 𝗶𝘁 𝘁𝗮𝗸𝗲 𝘁𝗼 𝗰𝗼𝗺𝗽𝗹𝗲𝘁𝗲 𝘁𝗵𝗲 𝗽𝗿𝗼𝗰𝗲𝘀𝘀.

Again, that depends on the immigration office you use. The reason you need between 15 and 21 days left on your existing stamp is the Non-O application goes under review for 2 weeks or more before you go back and get the new Non-O visa and 90 day stamp inked in. They put on your receipt when you apply what date you go back to get the "results".

𝟯. 𝗢𝗻𝗰𝗲 𝘆𝗼𝘂 𝗵𝗮𝘃𝗲 𝗿𝗲𝗰𝗲𝗶𝘃𝗲𝗱 𝘁𝗵𝗲 𝗡𝗼𝗻-𝗢 𝟵𝟬 𝗱𝗮𝘆𝘀 .. 𝘄𝗵𝗲𝗻 𝗶𝘀 𝘁𝗵𝗲 𝗹𝗮𝘁𝗲𝘀𝘁 𝘆𝗼𝘂 𝗰𝗮𝗻 𝗮𝗽𝗽𝗹𝘆 𝗳𝗼𝗿 𝘁𝗵𝗲 𝟭 𝘆𝗲𝗮𝗿 𝗹𝗼𝗻𝗴 𝘀𝘁𝗮𝘆 (𝗿𝗲𝘁𝗶𝗿𝗲𝗺𝗲𝗻𝘁) 𝗡𝗼𝗻-𝗢 ?

You can apply right up until the last day on that 90 day stamp you get from the Non-O <- BUT that is not recommended 😕 because if you're a document short you have no time left to rectify the situation and apply again. Most offices allow you to apply for an extension when you have 30 days or less left on your current stamp, SOME are 45 days or less. There's no down side to applying early because the ADD the year extension to the expiration date of your Non-O 90 day stamp (meaning you don't lose any time

𝟰. 𝗢𝗻𝗰𝗲 𝗮𝗽𝗽𝗹𝗶𝗰𝗮𝘁𝗶𝗼𝗻 𝘀𝘂𝗯𝗺𝗶𝘁𝘁𝗲𝗱, 𝗵𝗼𝘄 𝗹𝗼𝗻𝗴 𝗱𝗼𝗲𝘀 𝗶𝘁 𝘁𝗮𝗸𝗲 𝘁𝗼 𝗰𝗼𝗺𝗽𝗹𝗲𝘁𝗲 𝘁𝗵𝗲 𝗽𝗿𝗼𝗰𝗲𝘀𝘀.

You apply, you pay the 1900baht and you get the retirement extension inked in right then (except at Jomtien (and I believe Phuket) when you come back the next day to pick your passport back up