I'm not sure what you are asking. There is no such thing as extensions when it comes to the embassy. Extensions are done in Thailand at an immigration office. The embassy only deals with visas.
The 90 day non-O visa does not have an insurance requirement.
The 1 year non-OA visa (a completely different visa) does require insurance, as well as health check, background check and other requirements.
Are you actually planning on going for the 2nd 5 year? I read a report from someone who went to immigration with everything that should be required, including the 3 million in a Thai bank account, and they were flat out refused by immigration and told it's not possible.
I believe Tod Daniels said most people abandon the 2nd 5 years and go and get a new non-OX visa.