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Re: How long........
It's not a matter of break in to the country, but if the visitor has enough money to sustain him/herself. And according to the American Consulate, Americans can stay 3 months without a visa, 6 months with a visa. Then if you live here in Jamaica you can apply in Kingston for an extended stay with what they call Jamaica Residency. It is not Citizenship but allows you to stay lots longer (sorry I don't know how long but heard 2-1/2 years). You have to present proof of income coming in each month to show you can take care of yourself and proof that you own a home. After applying for that, and I don't know the waiting time, you can apply for Jamaican Citizenship. This does not take away from American Citizenship. You have a dual status. You cannot lose your American Citizenship unless you choose to give it up.
I feel that Jamaica is very loose with their requirements. America is way too stringent on who they let into the country. But that's another story.
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