Humour me here please. Rather than guessing an answer what is your passport country? I suppose I could dig a little and try to guess from your facebook profile, but it’s just generally easier if you state as such.
It certainly can be, but as it’s at the behest of an individual Immigration Officer then no one can say if it will be or not.
Generally they are looking out for people that may be “abusing” the visa exempt or tourist visa system by having back to back entries and maxing out their days with extensions and such.
If you have multiple entries of 7 days or so and then leave again it shouldn’t raise any red flags with immigration, but it’s no guarantee you don’t get an officer having a bad hair day…
Shouldn’t be an issue at all. Immigration Officers are well used to people travelling around SE Asia using Thailand as a hub. As long as you don’t have copious amounts of previous entries and maxing out your 60+30 days they probably won’t question you. If they do have proof of funds (20k baht or equivalent in cash) proof of accommodation (for a few days at least) and proof of a ticket out.
Depends on your previous entry history to Thailand. If you’ve had copious previous entries then you may well have an issue doing a bounce.
For a regular tourist with little or no previous history there shouldn’t be an issue, but as it’s up to an individual IO to decide then there are no guarantees.
Usually you’d just need to show proof of a double entry to show the need for a multiple entry visa.
However now that you get 60+30 days per entry the need for a multiple entry visa is questionable. A single border bounce will give you up to 180 days in Thailand if you qualify for visa exempt.
If he gets the DTV then you can apply for one as a dependent. Depending on the embassy or consulate you use you may or may not be required to show 500k in a bank in your name. You’d need to check their website for specifics.