section 2 applys to those 'Already in Thailand' on a permission to stay. Meaning if your already in Thailand on a 12 month stamp or extension, you won't need to rush up town and buy insurance. It doesn't apply to entering.
yes I don't think there is any doubt of the process applying for visas on or after the 31st October. It's previously issued visas that is questionable in how it may be applied.
The more I look at that form, the more it appears that it's a form to obtain a new O-A visa using a non Thai insurance company. I don't think, but I've no problem being proved wrong, that it is for proving you have a foreign health insurance policy when entering Thailand on a previously obtained O-A visa that has no Insurance annotation marked on the visa. Just my thinking but I'm edging towards a Thai Insurance policy going to be needed on O-A visas issued BEFORE 31st October.
There is mention in section 3 of the police order about buying Thai health Insurance before being allowed entry if you don't have insurance. I'm 100% certain there is going to be Health insurance agency's at the airports at least in order to buy insurance.
The visa for entry to Myanmar is bought on the jetty at Kawthuang. Its a day pass and is only good for entry to Kawthuang. You cannot go travelling in to Myanmar with it.Your stamped out of Thailand first before you leave. You cannot even be in Myanmar waters without a visa
I am confused with exactly what your asking? Your going by boat but coming back by land. Most boat trips will take you to Kawthaung. Not sure what you will going there for. But anyway, you cannot get a Thai visa in Kawthuang. You would be coming back into Thailand visa exempt. If you have already done 2 visa exempt land entry's this year, you wouldn't be able to do it.