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LordHawHaw

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Tons of questions, few answers, I see.

Visa: a friend from South Africa lives in the south, goes every month to the Malaysian border and comes right back.  He's a 30 day tourist, period.  Lives in a house he and his girlfriend bought.  He has done this for years and there is no end in sight.

A work permit is not easy if you want to work in a pub!  You have to invest in a Thai business, which can be arranged (boy, can it ever!).  I was advised seriously by a local man who is experienced in such things NOT to do it, as it means you incur liabilities that do not exist under US corporation law.  I suspect Irish law is similar to US law as regards liabilities.  Be careful.  You are in a nation that has no tradition of common law and takes a paranoid and predatory view of foreigners.

Marriage here can get you a Non-Immigrant "O" visa.  That may be helpful.  You must register at an Amphur (spelling?) office to make the marriage legal.  I am informed that your wife may now own land, which is a new development that I am not sure I believe to be true.  Keep in mind that some farang registering marriage officially have in past years reported serious foot-dragging at some offices, and that you may register at any office in Thailand, regardless of where you were married.  If stonewalled, go elsewhere.

Seriously suggested: read ALL the other posts regarding marriage, girl friends, dowry, and so on that you will find on this site.

Second very serious suggestion: go back to the above sentence and READ IT AGAIN.

In view of your financial circumstances, your best bet is to stay until the money runs out, have a good time, enjoy life with your enjoyable girlfriend, and then go home, where you can make a living.  IMHO.  You can always save up, come back, get another enjoyable girlfriend, and so on....and on.

In general, I think most experienced farang here would advise you to go slowly, keep your money in YOUR hands, be aware of the fact that you are viewed here as very wealthy and that you will come under pressure to be generous, and try to establish candid communication with your girlfriend.

A prolonged stay and even Thai residence are possible, but certainly easiest for those whose financial resources are, frankly, greater than yours as you describe them.  Personally, I would not attempt to get any papers or status that are obtained through the use of "tea money," as that merely leaves one vulnerable to extortion.

Good luck.

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