in case Immigration wants to see a certified by your embassy document telling them that you have been issued a new passport, try to evade it by politely saying that your embassy does not issue such a certification anymore (a new passport is a new passport!)
you need nothing but your old passport and the new passport. And maybe the printed TDAC to show (if it applies). Immigration will transfer only their own stamps - which in your case would be the "extension of stay permit" stamp and the re-entry permit stamp (in case you bought one). The "visa" itself cannot get transferred, the visa itself is a separate .pdf document. And if you entered on the new passport, the entry stamp will already be inside the new passport
this depends on the embassy where you apply through their E-Visa System. Some accept an up-to-date statement, others want to see 3 months of account statements, and others want to see 6 months of bank statements
you don't need any health insurance if you apply for the 90-days Non-Imm-O Retirement Visa, - everyone for him/herself. Each one of you needs 800,000 THB equivalent in your home bank account for the application to the visa itself. After having entered Thailand, each one of you needs to open his/her own Thai bank account in your sole name (!!) as soon as possible, and transfer the required minimum of 800,000 THB onto it. As soon as the money has been sitting in your two accounts for 2 months, you can apply for the "1-year extension of the stay permit based on retirement" from the 90 days stay permit to a 1 year stay permit. You can only apply on Immigration if you got a valid TM30 accomodation registration, otherwise Immigration will not service you. Some Immigrations accept a hotel stay and the hotel's TM30
AFAIK a TRN code (Transaction Reference Number) points to some message that was sent along with a SWIFT-transfer. It is not the code of the transaction itself
are you 100% sure that these WISE transfers are still coded as FTT (or FET) in your passbook as coming in from abroad ? There were reports that many are now coded as inner-Thailand transfers. You better update your passbook and check!
Unfortunately, you wording is wrong. The non-O visa itself expires when you enter Thailand on it. You receive a 90-days stay permit when you enter Thailand. You must apply for the "1-year extension of the stay permit" before the 90-days stay permit expires, the soonest being the day when your 800,000 THB deposit in your Thai bank account has been sitting in the account for a minimum of 2 months
"I am entering Thailand on a 90-days single entry Non-Imm-O Retirement Visa, I shall get stamped in for a 90-days stay permit.
And will hopefully be converting this 90-days stay permit to a 1-year Extension of the Stay Permit based on being over 50/Retired "
NOTE: you do not convert to any “retirement visa”. The visa becomes invalid and “used” upon entering Thailand. Sadly Thai Immigration does not draw a difference between a stay permit and a visa. For them, in their inaccurate English, it is the same thing
And regarding your question: On a 90-days single entry Non-Imm-O Retirement Visa, you won’t be asked for proof of onward travel or a return ticket, by the airline.
If the check-in crew at the airport starts asking for this, demand to speak to the manager. As this Non-Imm visa-class is meant to get converted to a long term stay in Thailand, so there is no return ticket needed