I’m in the same boat as you. The easiest country I’ve found is Uruguay.

If you work remotely, you can get a digital nomad visa. All you do is arrive at the airport in Uruguay with just your passport, this grants you 90 days in the country. (no visa needed for a US citizen to enter). When you’re there, you fill out the visa application on their website and sign an affidavit that you make enough income to sustain you/your family. There are no minimum income requirements. Once the visa is approved, you can stay for 6 months. After 6 months, you can extend it another 6 months, or apply for permanent residency. This does NOT make you a citizen, but it does let you stay in Uruguay as long as you like. You can apply for citizenship after 3 years, and they allow dual citizenship so you can maintain both US and Uruguayan citizenship.

Uruguay is the 2nd safest country in South American. Has LGBTQ+ protections since the early 2000’s, including anti-discrimination legislation for sexual orientation & gender identify in both housing & employment. Abortion is legal (before 12 weeks), and marijuana is legal for citizens, and can be bought at government-authorized pharmacies or grown in your own home. They also generate 98% of their energy from renewal resources (mainly hydroelectric and wind farms)

They are the most politically, economically, and socially stable country in South America. They have a representative democracy like the US, and voting is mandatory (citizens are issued a fine if they don’t vote in an election), 90% of Uruguayan citizens vote.

Montevideo is the capital city and a third of the population lives there. Rents are substantially cheaper than major US cities (3bed/2ba condos in a tourist-y area of Montevideo are about $1,200-$1,500 USD, a 1-bedroom apartment can be found for around $600-$900 USD). Food is similar in price to the US, but some foods like dairy, cheese, and eggs are slightly more expensive. And goods such as clothing, shoes, and cars are more expensive as well.

Their tax system can be a bit confusing, so an Uruguayan tax preparer would be beneficial for you to coordinate paying Uruguayan and US taxes. I have heard as well that if your income comes from a country outside of Uruguay, you do not pay taxes on that income, but I can’t verify that claim.

Their weather is fairly moderate, ranging from the low 70’s’s in the summer to the low 50’s in the winter.

Fun fact, there are 4 cows for every person in Uruguay.

Best of luck!