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New non-o marriage in/out back in and stay


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Hello all .  in need of advice/ direction..  will be doing my first  non-o visa based on marriage  - to Thai wife,     ( bringing the  wife home after  12 years in the USA )

we will be entering with  my non o visa,  wife ( USA Citizenship  & Thai National will enter on her Thai passport ) and my son will enter with USA 30day exempt ...   I would need to escort him back to the  states after 3 weeks ,  then  pretty much turn right around and come back into Bangkok..   the questions I have ,,   do I just get a  single non o and use a re-entry permit,,  or get a multiple ?  I do not plan to be going in/ out after this,,,  I pretty much just want to get into the  "system" and do my extension based off marriage and be done with all the  fuss.   does the  initial entry count as the  starting point counting to do the  extension? or does the  clock reset when I get back ? Already have  bank acct / drivers licence(s) and health insurance... will not be working (retired)  age 64 ...   any advice is well appreciated..   thank you

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