Not sure how many start up entrepreneurs will be making 200k a month too quickly ;) For the I visa, you need to invest 20 million baht, damn that is a lot......I guess these are all just steps towards a higher quality of expat in Thailand with money and insurance. Fair enough too..............Great visa options though. No work permit.
6 month multi entry tourist or 60 days tourists, but not a good long term strategy. Or send 800k to a bank in Thailand and leave it there. Get a 90 day NON O and then enter Thailand. Extend for a year and get a multi re-entry permit. Come and go when you want. Extend every year while in Thailand.
So in your post you state that insurance is needed for an OA and ask about it, and then in the comments you state that you have a NON O. Why ask about insurance for an OA if you don't have one??