I have worked with a few guys who live in the Philippines or Thailand, and a couple guys who live in Vietnam or Japan.
I know people who bought winter home small farms in New Zealand many years ago. However, New Zealand has become very expensive and expats are leaving. Australia is similar.
I know people who live or have lived, or have second homes in various places in Europe.
Latin America is the favorite place of Americans and Canadians to live. Mexico is easy, you can drive there, flights are short, and something like 2 million Americans and Canadians live in Mexico. It’s not as cheap as it use to be. Costa Rica is nice but it can be expensive to live like an American in the desirable areas.
There is a lot to be said for Europe. Outside of large cities and the most desirable resort areas it’s not that expensive, particularly in Spain and Portugal. Even rural France is affordable.
A Schengen tourist visa gives you access to most of Europe for 180 days per year. 180 days a year is easy in most of Latin America.
It’s fairly easy to live in most places for a few months. Rules change often which make it easier or more difficult to live in some countries. Digital Nomad visas are popular right now. Some countries restrict the purchase of property.
I encourage anyone to travel and check out a few different places. If you are thinking about putting down roots somewhere, live in a “short term” furnished apartment for the first year. Foreign property can be easy to buy, but very difficult to sell.
The safety and comfort situation is subject to change. Weather is a huge and changing factor. Some places are great in the winter, but suck in the summer, or vice versa. Some places are suffering from over tourism and too many foreigners. Some places are experiencing droughts or wildfires. Some Latin American countries are very stable, others are one election away from becoming Venezuela.
I try to stay away from places that have cruiseship tourism. They become ruined and are a ripoff.
The expat and digital nomad websites have lots of information, but they tend to be very rah rah promoters that want to make money helping you relocate. They don’t reveal the negatives. Be very wary of YouTubers.