Comments by "Jeremy Barlow" (@jeremybarlow2291) on "US Visas for Caribbean Citizens" video.

I think the more interesting question for an American obtaining a Caribbean CBI is how easy is it to obtain a Canadian visitor visa. I know the typical Canadian visitor visa is a multiple entry visa that allows many trips over 10 years and if you can obtain a residency permit in Mexico for your Caribbean CBI, there are enough direct flights from Mexico city to Vancouver, Toronto, and Montreal to allow you to transit to Europe from Canada without having to obtain a US visa if you can visit Canada. I ask this because unlike obtaining a visa for the US you could at least theoretically arrange a Mexican residency permit for the CBI before renouncing and also obtain a Canadian visitor visa for the CBI before renouncing and if you can visit Canada and reside in Mexico at least part of the year, even if you cannot obtain a US B1/B2 visa or with Grenadian citizenship an E-2 nonimmigrant investor visa you could still fairly easily visit US relatives who have visa free access to Canada or Mexico in those US neighbors. Having Canada as a transit option on their 10 year multiple entry visa would not be a bad thing to have either before renouncing. Sure Sao Paolo, Mexico City, Panama City, and St Maarten provide pretty good access to Europe, Africa, and Asia, but Toronto, Montreal, and Vancouver are not the worst places on earth to be able to transit through.
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If you are earning enough "passive income" which could be dividends or distributions from your own business Portugal, Argentina, Ecuador, Costa Rica, Nicaragua, & Mexico spring to mind as departure points for residency and potential citizenships. If you are a freelancer, Germany, Spain, Croatia, or the Republic of Georgia may provide a path to residency and citizenship. If you can teach English, Japan, South Korea, Taiwan, and Thailand may provide residency permits, but the path to citizenship is much more difficult. Figuring out how to operate a location independent business that brings in at least $2k to $3k a month is your best bet for making an exit long term.
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Tax savings are not the only reasons to renounce. Opposition to the empire is reason enough for many people, but familial relationships can be harder to severe than citizenship. Having listened to Andrew's comments over the years, I suspect US adventurism abroad was one of the many reasons he decided to renounce and if may have been the primary fuel for his initial departure.
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@choreomaniac Roger Ver was convicted of a federal explosives charge as a young man dealing with fireworks charge before obtaining a CBI from St Kitts & renouncing US citizenship. He established residence in Japan and he has a B1/B2 visa to return to the US, so it is not impossible to obtain one. You need to establish ties to your place of residence. You need to have the economic means to provide for yourself and evidence that returning to your place of residence will be likely. Renouncing your US citizenship & establishing citizenship and residency elsewhere is I dare say stronger evidence than most would present that you have no plan to illegally immigrate to a country you emigrated from and established a life elsewhere from. As Andrew has pointed out he paid in the single digits in taxes to the US and elsewhere before renouncing. While no longer being required to fill out a lot of forms and no longer being barred from investments that the SEC regulations made impossible overseas were part of his reasoning I am sure, taking up citizenship in a Commonwealth country that you have no tax obligation to and which has no standing army is very different from being a citizen of a country that has been at war every year of most of its citizens lives, especially when those wars were fought halfway around the globe.
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@choreomaniac Going back to the US 3 to 6 months out of the year would be entirely different to the reason to obtain a B1/B2 visa which would be primarily I think added transit options between Europe & the Americas, but also the occasional visit of maybe a few weeks to see family, or attend a funeral.
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@choreomaniac Yeah I was thinking more from a genuine pragmatic prospective of someone who is actually likely to renounce. Even with reason far stronger than merely tax planning, taking the step of renouncing is a big one. I doubt I would return much, but pragmatically there are funerals I would have to return for and there are some other events that would require return trips and having looked at how difficult it can be to route from almost anywhere in the Caribbean to Europe without a trip through the US from a practical standpoint there is a reason to want the multi-year multi-entry B1/B2 just for transit purposes.
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Depending on how you receive income & how much you are making ie remote work, investment income, time to citizenship, a host of criteria really, obtaining a residency permit in various EU jurisdictions may be beneficial or practical. I mean most EU countries, not all, but most, allow dual citizenship. If you have $1 million to invest your options are different than if you are living paycheck to paycheck. Your options are different if you are earning an income from rents and royalties than having a job that allows you to work remotely from anywhere. Of course that job's definition of anywhere may change if your location impacts their tax residency and reporting requirements. There are a lot of variables that must be considered. An EU citizenship gives you a lot of options for places to live in Europe long term, but using your days inside and outside the Schengen zone properly if you are nomadic can allow you to potentially live all over Europe without ever being a resident using only tourist visas. How long this will remain the case may remain to be seen as the tax world and the labor enforcement rules race to catch-up with the new remote work reality.
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