There's no way to qualify for a retirement visa with 33k baht per month.
And all of that is irrelevant because the only way to use income in Thailand to apply for your extension is with embassy certified income. The UK embassy does not offer this for many years already. That means your ONLY option for the first year is 800,000 in your Thai bank account.
If you cannot meet the requirements, your only other option is paying an agent who will then "pay" immigration to look the other way.
No. There is no rule or law that says any number of days. It's at the discretion of the immigration officer you are standing in front of. Whatever their personal rule is. Many people have experienced issued if already at 90 days within 6 months and 6 months within a year.
This is not something anyone here can answer. This is a question for his employer and his immigration office. They are the ones processing everything, it's up to them on when it's all completed.
It's not a rule. But a lot of people are being warned they are coming too much as a tourist and they will not be allowed back again without a long-term visa.
That's not true. There are agents you can purchase "safe entry" from that will vet your information with immigration officers at the airport, who will then meet you when you get off the plane and walk you to the immigration counters, open a counter just for you, and stamp you in. Guaranteed entry starting at 2000 baht and going up to about 8000 baht depending on your history.
get the non-O in the US. You won't be able to get it in Thailand without a Thai bank account and you can't open a Thai bank account without a non-immigrant visa. So you have to get the visa from the embassy