There is no multiple entry non-O visa. There is a 90 day single entry non-O visa and a 1-year extension. The last embassy that offered multiple entry for non-O visas was only for marriage, not for retirement, and they stopped on January 1st when all embassies worldwide switched to e-visa.
You do something that qualifies for DTV, such as remote work, or a soft power activity like Muay Thai, cooking school, or medical procedures. Then you leave Thailand without a re-entry permit to cancel your retirement extension and apply for the visa at a Thai embassy.
Honestly, it doesn't really matter. If you put it to match your passport it will be fine, and if you put it to Thailand once they add that as an option before it's deployed.
There is no such thing as a 12 month non-O multiple entry visa.
You have to get a 90 day non-O visa, which is single entry. Then once you are in Thailand you open a bank account, transfer the required funds (800,000 baht) within 30 days of arriving to Thailand, and then after the money has been in the bank for 2 months, you can apply for the 1-year extension (not a visa anymore, an extension).
Once you're on the 1-year extension, you can apply for a multiple re-entry permit. That does not make your extension multiple entry, it makes it multiple re-entry. Multiple entry is a completely different thing.
What a re-entry permit does is keep your extension alive if you leave Thailand. So normally if you left without one, your extension is cancelled as soon as you leave, and when you came back you would have to return as a tourist and start all over.
With a re-entry permit, your stamp stays alive, but you do not gain any extra time, and the time keeps ticking while you are out of Thailand.
So if your extension ends July 30, and you leave on March 30 with a re-entry permit, and then return on April 30, you'll be stamped back into Thailand until July 30th. If you're not back in Thailand before July 30th to apply for your next extension, you would lose it and have to start over.
The non-O visa does not have an insurance requirement. You are free to choose any insurance you want.
when was the last time you converted from tourist to retirement including adding a bank account? Because it's expensive now. And even more so over the last month
When you first land you'll get 60 days visa exempt, not 30. And it's not a visa, it's visa exempt.
Then you'll get converted to a 90 day non-O visa, not an extension. And also a 12 month extension at the same time because that's how agents do it. So 15 months all at once.
No, it's not possible. Because it's not a 15 month visa. It's a 3 month visa and then a 12-month extension.
The conditions are that you give the agent a lot of money and they get you the visa and extension. And if you don't have your own money in a Thai bank account for this visa, then you'll have to pay an agent again next year because you won't meet the requirements this year and they'll check on that next year.