Of the insurance you’ll need a police background check and a medical certificate you’ll be stamped in each time you return to Thailand for one year or as long as your insurance is good for during the validity of the visa after that you’ll be required to show the funds in a Thai bank to extend plus you’ll always be required to have insurance
you should be fine doing bounces as long as your not maxing out your stay each time my neighbor works in the North Sea and has been coming and going for at least 16 years no problem