I don't mean to pry, but if you have a million baht and are 61, why not just put 800k in a bank and live off the 'retirement' extensions (yes yes I know not the right term, but commonly referred to as this) for the next 20 years at 1900 baht a year. That would be 38k baht instead of a million. Especially considering that a lot of people don't live until 81.
As far as I know, that is not correct. There is no penalties for children under 15. I believe that includes fines or overstay stamps. So in other words a child does not need a visa at all until 15.
Yes that is correct, and is what I am referring to. Start the process over again with his wife as the retiree :) She already has the money in the bank in Thailand, so easy, and as mentioned, no insurance.
If they won't give your wife an extension, then get her a 90 day Non O and then extend that later, ie effectively starting the process completely again for her and separating it out from being your dependent. That is, if you go tomorrow and they say the same thing.
No one can answer this question. To lessen the risk of problems, get a tourist visa. If you are worried, on arrival, it is advised to have 20k baht or same amount in other currency, an onwards ticket or return ticket, an accommodation booking (tourists don't have rental agreements)...even a booking that can be cancelled is fine.