If your re-entry permits expire in JULY and you will return in SEPTEMBER then you will need to start again. Either get single non-O's out of the country or convert your new entry once you arrive. Not a major issue but a little more than just getting new extensions.
It does get boring here I can do about 5 months max then go to Vietnam, Colombia, Brazil, etc. It's a good home base b/c it's inexpensive and the Thai's are mostly friendly but that's about it.
I pick the phone up to answer a msg, check a sports score and then end up on here. It's wasting life but so hard to stop.
Nobody looks back on a weekend/month/year and thinks...what a great time that was, if only I spent more time on that forum.
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