Yes, if you want to apply for an initial in-country Non-O visa based on retirement, you have to prove your funds are internationally transferred. That is in the requirements (police order).
You can also apply for a Non-O single-entry for 90 days in a neighbouring country or before you fly to Thailand, to enter Thailand on it.
Not anytime. Depending on your local office, you have to wait until you have
*****
days or less remaining at the earliest.
Most offices accept 1-year extension applications within the last 30 days. There are some offices, such as Bangkok, Chiang Mai, and a few more, that allow you to apply for it when you have 45 days or less with your stamp.
You can apply for a 30-day tourism extension first, then apply for an initial in-country Non-O visa.
Be careful to counting remaining days if you want to get a 30-day extension. Chiang Mai has a policy of remaining days of stamp that is actually 15 WORKING days, and there are several holidays December - January.
As you entered on a visa-exempt, you can just forget about that part.
That stamp is used for ANY extension of stay, including long-term ones, and generally means you need a re-entry permit if you want to keep your current permitted stay stamp "alive" when you make a trip to another country within the period.
A re-entry permit wouldn't give you any extra days than the current stay stamp (in your case, 5 Nov). And I don't think immigration officers would sell you a re-entry permit on a visa-exempt entry stamp.
You just leave Thailand by midnight on 5 Nov, then you will be fine.
Very good of you to read the stamp carefully and try to clear any uncertain points, which many people don't do often, then go into some trouble later.
You can apply for a re-entry permit at the "re-entry visa" counter on the day you leave, after check-in and going through the security check. The counter is open
****
.
The easiest is going to the International Departure Gate 2. There is a counter on your right when you go down the escalator after the security check. If you go through another departure gate, you tell the officer at passport control you need a re-entry permit, then go all the way to the re-entry permit counter at Gate 2 from the airside.
You may want to add 15-20 minutes to get one. Sometimes several people are waiting. When no one is waiting, it may take a few minutes, but it may still take about 10 minutes.
The official fee is the same, 1000 baht for a single re-entry permit, 3800 baht for a multiple re-entry permit.
If you don't have a photo (passport size), you may be required to pay an extra service fee of 200 baht.
No, if you enter Thailand on a visa-exempt for 60 days, you cannot apply for an in-country initial non-O visa based on being over 50/ retirement without a bank account in Thailand unless your embassy in Thailand issues an affidavit of income. You need 800K baht in a Thai bank account OR an embassy affidavit for an initial visa application at the local immigration office.
If you want to open a bank account for an extension, you need to enter on Non-O retirement issued from the Thai embassy/consulate outside Thailand.