pull the black and white blinders off for a minute and remove the fact you feel the OP is an expert in Visa language like yourself. He wants to accomplish a retirement option inside Thailand and have the ability to leave and re-enter Thailand. Now he can come here as a tourist like most people do and begin the process for a Non-Imm O with no insurance required. Once he gets his Non-Imm O he can pay the extra 3800 baht and get a multi entry stamp. Just accomplishing the goal without going the path you feel his words restrict him to.
Elite doesn’t offer anything substantial as you are still in a tourist style visa arrangement just like Non-Imm O. May give you some discounts on food and hotels at the high levels but nothing special to spend the money on in my opinion.
There is currently no limit on how many times you renew a Non-Imm O. Each year is a new application. The only difference between the 1st application and follow-along applications is that the full amount of money has to be seasoned in a bank account in your name. After that you can use the 12 month transfers as qualification.
or you could get Non-Imm O inside of Thailand and renew every year. Add a multi entry stamp at the same time of extending for an additional 3800 baht. It seems more people are on here to tell you what you are wrong about instead of finding a solution or answer to the question as you word it. 🤦♂️