okay, so it should be easy peasy to apply for a 90-days Non-Imm-O Family Visa through the online E-Visa system of a Thai Embassy in a neighbouring country. You need to fulfill the financial proof. Either a minimum of 400,000 THB in a Thai bank account in your sole name, or an income affidavit of your embassy in Bangkok.
don't try to call. Send an email request. And check their website about what they say about their processing time. And don't forget, January is High Season, the embassy might receive more applications than in the low season
I would leave the 400,000 THB in the account during the 4 weeks "under consideration". After you have been issued the 1-year Extension, you are free to use the 400,000 THB for whatever you think is good
three weeks of time for the processing of an application to a single entry tourist visa throug the The Hague Thai embassy, should be tight, but enough. Why not send an email enquiry to them now, asking exactly this question? They can surely tell you if the timing will succeed or not
most Immigration offices allow the application to the 1-year extension of the stay permit up from 30 days before the expiry of the 90-days stay permit you got stamped when you entered Thailand. Some Immigrations like Bangkok, Jomtien, Chiang Mai, Khon Kaen and others I don't remember, allow it up from 45 days. If you want to know how "your" Immigration interprets it, you need to visit them and ask and also politely ask them for the list of requirements for the application to the "1-year extension of temporary stay permit"
maybe some embassies have changed their requirements, and ask for a 90-days travel insurance for the first 90 days of a stay permit you get stamped in when you enter on this visa-class. If you have a valid link or a valid official mentioning, then PLEASE link it! . . . . For a 1-year extension of the stay permit based on retirement/over 50, there is no mandatory health insurance - that's a fact
if you did 12 years of extensions, and never needed an insurance, you obviously started out of a Non-Imm-O Retirement Visa. . . . this means, NOTHING has changed so far. There is no mandatory insurance for extensions of the stay permit out of former Non-Imm-O Retirement visas