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I knew someone who did this to andorra. There were a variety of drawbacks, including only being able to send like 30 days per year for 10 years here, and is supposed to file taxes for 10 years. I know if you just reside offshore you are exempt from taxes on like your first 80k or so.

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Hey. I live offshore now. Do I get the first 80K of my gambling wins tax free? or is this only for money already being taxed by another country?

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I haven't read the responses yet, but I know this: talk to an accountant with experience dealing with US expats in your country.

Edit: After reading all the responses, I believe this even more-- see a professional in Thailand that specializes in US expats. If he has experience with pro gamblers that would be a big help as well. I don't think people should cheat on their taxes, but I also don't think that they should pay more than their share. (For example, you may be able to defer/eliminate taxes on a portion of your income by declaring yourself a pro and contributing to a retirement account. I don't know, I am not a tax pro.) In any case, it will be worth the fee.

Also I agree with the other posters that you are underestimating the value of being a US citizen. Of course it is your decision to make, but if I were you I would take my time and talk to alot of people I trust about it, including your parents. It is a decision that will affect you for the rest of your life, and you are a young guy (I know you must be tired of hearing that, but you are young). If you wait two years to make a decision it won't kill you, and even that amount of time will give you a significantly better perspective to make your decision from. You don't want to make a decision that is good for the 19-year-old you and bad for the 25-to-75-year-old you.

Best of luck.