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People often ask me which country they should expatriate to. Here are my answers:

1. Wherever you have close friends/family.
2. Wherever you can get an easy citizenship.
3. Preferably both.

Expatriation is a life choice for cranks and vagabonds, not normal people.
It's easy to look at the Big Mac Index or Numbeo's Cost of Living Map and think, "Hot damn, I'd save SO much money if I moved to Kiev/Manila/Timbuktu!", but moving abroad for better weather or to save money on rent ignores the mental/spiritual aspects of pulling up roots.
First, many second- or third-world countries have shit infrastructure, even for the rich. The tap water might be poisoned. The traffic might be horrible. The restaurants may be staffed by mouthbreathers who habitually forget to wash their hands after taking a shit.
Ex: I was once waiting in the airport of Davao City in the Philippines and I watched ALL of the tap water in the building turn brown. Even the water in the toilets was brown. Brownouts and blackouts are common, Internet service is spotty. These inconveniences add up.
In Ukraine, I was told by every landlady/lord I ever had to not drink the tap water because it was poisoned with heavy metals. I once got stranded on a train in December because it was a Brezhnev-era locomotive with USSR insignias and it was on its last legs.
One or two problems you can handle. But can you handle dozens of them all the time? Simple things like buying aspirin or mail delivery are like pulling teeth outside of the first world. If you want to expatriate, you have to have a supernaturally high tolerance for bullshit.
Second, there's the loneliness. You've got family and friends, and if you move abroad, you'll probably see them once a year at most. You need friends where you're going. If you don't have them, you need to make them, which is a struggle for more introverted people.
Your potential friend pool consists of two groups: locals, with whom you'll have to learn the local language and navigate local customs, and other expats, who are very likely to be the kinds of annoying shitbags you're trying to get away from. Pick your poison, motherfucker.
And yeah, most expats are awful people. In Ukraine, it's sex pests. In Southeast Asia, it's old sex pests. In Hungary, it's British stag partiers and old German sex pests. In Poland, it's American backpackers. In Georgia, it's douchebag "digital nomads." Have fun!
The happiest expat experience of my life was in Budapest, because I had friends there before I moved. They helped me get set up and it was nice being able to call them up for a drink whenever I was ready to mingle. In fact, they were the reason I moved there in the first place.
Third, there's residency and citizenship. Both are very difficult to get in many places unless you have a local job (and are getting paid a shitty local salary). That relegates you to living on short-term tourist visas or "visa-free" regimens.
Most countries allow Americans generous visa-free travel privileges. Even Russia offers Americans a three-year tourist visa. But you can't build a permanent presence in a country off a tourist visa. At some point, you need to normalize your presence with residency/citizenship.
That's why the best country to move to is one where you can easily claim a citizenship. Many European countries offer citizenship by jus sanguinis (right of blood), meaning you can become a citizen by proving your ancestry. Italy, Ireland, Poland, and Croatia are among them.
Latin American countries are more generous than European ones when it comes to immigration. But again, do you have the patience to live in, say, Ecuador full-time? Also note that many countries where citizenship is easy to acquire (such as Georgia) prohibit dual citizenship.
Fourth, even if you can put up with bullshit and integrate into your new country, you'll never feel 100 percent at home. You may think America is dumb and gay, but you've been marked by American culture regardless, and relocating abroad WILL be a shock to your system.
This is particularly pronounced if you're white and move to a non-white country. In Thailand or the Philippines, you will always be seen as "the white guy" no matter how long you live there and how well you acclimate to the culture. No getting around it.
Remember that French-Canadian dude who got busted in Thailand for running a dark web market a couple years back? That guy learned to speak Thai, married a Thai woman, had a child, but he got popped almost immediately because his neighbors ratted him out for being a farang.
In a European or Latin American country, you can blend in better, but there are still aspects of foreign culture that you will likely never get used to. Even if you marry a local, have kids, and never set foot in your home country again, you'll always be an outsider looking in.
My decision to expatriate was based in part on the fact that I've spent my entire life moving around. When I turned 18, I left my shithole city in upstate New York and never looked back. The longest I've ever lived in any city as an adult (Albany, NY) was two and a half years.
Living abroad is fun and cool. You get to see parts of the world and do things that few people do. But it's not a panacea or a replacement for a happy home life. If you've got a loving family, great friends, and a good job at home, don't give that up to become an expat.
Many expats are freelancers and/or have online businesses. They can make money anywhere they can connect to the Internet. The other option is to get a local job, but local jobs pay local wages.
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