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Multiple-entry TV and health insurance / upgrading from TV to Non-B to become a teacher

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Hello,

 

I used to teach in Thailand. I want to go back. Just curious about a few things.

Because health insurance is necessary now, how does this work with multiple entry tourist visas? Is it possible to even get one now? 
Also, I would like to teach in Thailand again. As someone who currently lives outside, can I come in with a single-entry tourist visa, sign a contract, and upgrade without having to leave a country?

 

Any help would be greatly appreciated.

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