yes, as far as it concerns an old O/A. So any extensions of stay (meeting the requirements financially, like she does) out of an old O/A now are under scrutiny in Chiang Mai and need a tgia listed insurance? Well she should eventually do how she was advised, exit and let the O/A become invalid, enter with exempt visa and apply for the conversion to the Non-O

and for all subsequent renewals of an extension of stay (EOS) based on retirement out of an old O/A you will require the Thai insurance. It doesn't make sense but this is the rule. Only when the EOS is made out of a Non-Imm-O, there will be no insurance requirement (however it is always good and makes sense to have one for a longstay in Thailand!)

if you are worried about the Airline in Vientiane does not let you board because you have no onward ticket out of Thailand within the first 60 days of your Tourist visa, just follow the advices from above and book a cheap throw-away or able to cancel for free ticket

you can set up the online registration when you are back at home, on a PC (which i recommend) or on the mobile phone. Ask your wife to sit with you, open the registration process page and follow step by step. After completing and submitting the data, you can expect a reply and login data within hours/days after submission, and will be asked to change your password, again. At some points the registration process is a bit tricky, you will need to be able to read Thai, that's why I suggested have your wife sit at the screen with you. The next page is the link to the registration page. note it says it is for hotel and guesthouse, however it is also good for private people

you do not report in Bangkok as you don't live there. If your wife's house is in the area served by the Kanchanaburi Immigration office, this is your place where you register the TM30. And all of the World's numerous confessions have to register within 24 hours of arrival in Thailand, not only Muslims . . .

if you make it to Immigration within the 24 hours of arrival in Thailand, the night at your daughter's condo does not count. As you have time until 6pm on January 16th for the registration at your wife's house before Immigration office closes. Just make sure you get her accompanying you, have all documents in row, which is wife's blue housebook, wife's ID, your passport and departure card, copies of each signed by wife, copies of picture page of your passport and visa stamp page of passport, signed by you. If in hurry, go have the copies made at immigration

I was able to register the Girlfriend's house and receive a password only 2 hours later. YES, the filling out is VERY tricky . . I surely understand a lot of people fail with this. You MUST have a thai speaking & reading person siding you when you fill it out for the first time (unless you are capable of reading Thai)

so, assumed one was not self employed, quit his paid job in order to enjoy a 6 month holiday in SEA. He cannot supply a current proof of employment but he can show a tax statement of the previous year. Would this suffice the requirement? I guess, best bet is to ask the embassy or consulate by phone or email