There a numerous ways to obtain a visa based on retirement. I can only relate the way I used. Enter thailand on visa exemption, passport only, the same as going on holiday ,valid for a fixed period of 30 or 60 days depending on the law at the time. I then used an agency to facilitate the visa. The reason being you need a thai bank account with
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0 baht in the account for a period of time before applying for the visa. The thai banks will not issue a bank account without the visa, and no visa without the bank account. The agency applies on your behalf to the bank for an account with the intention of gaining a visa. After you have deposited the money in the account and received your visa based on retirement, when the time comes to renew (extend), the visa, you can visit that immigration offices and do it yourself.
Don't worry too much about upsetting people on this site. There are many good, decent people here and a minority of inconsiderates. The majority of decent people are here to help and obtain help when needed, they will understand and take it for what it is.
A good question. Never spend more than you can afford to lose or walk away from in Thailand. This means that you should have somewhere in your home country to come back to if it all falls apart in Thailand.
I came to thailand with the same dilemma. I bought a return ticket, was not asked for confirmation by anyone, canceled the return when I obtained my visa extension.