Question: of all the places you've visited, if you had to settle down in one location, where would it be?
I think it's inevitable that you compare every new place with where you used to live. Toronto has many great qualities like low pollution, low crime, familiar culture, all our friends/family live there. The drawbacks are that it's too cold in the winter, the traffic is horrendous and it's very expensive to live in the city.
Right now we're bound by cost. If we got amazing-paying jobs or won the lottery, there are some perfect places to live in Western Canada and Europe, but as of now they're out of our price range. If money were no object we would move to Vancouver Island in a heartbeat. All the benefits of Toronto, familiar Canadian culture plus warm winters, and we have so many friends in the area. But it's as expensive (if not more) than Toronto.
In Europe, we'd live in Ticino in southern Switzerland for sure. If we were stinkin' rich... Great standard of living and temperate Mediterranean winters, and the ski hills are not so far away. Everyone speaks Engish, Neda's sister lives an hour's drive away in Milan, and we have soooooo many friends in Western Europe that are less than an hour's flight away. €50 will take you pretty much anywhere on the continent with RyanAir.
But realistically if we were looking to retire on a meagre pension or stretch our savings for as long as possible, we'd probably settle somewhere in Latin America. I've learned enough Spanish to know that I could probably pick it up if I applied myself.
La Paz, in Baja California was a really nice upper-middle class city, but it gets really hot in the summertime. There are some colonial towns in the Mexican highlands that are also liveable - Ajijic and the Lake Chapala district are very ex-pat friendly with the perfect temperature all year round. Oaxaca is also nice; bit more happening, not as sleepy as Ajijic.
In South America, we stayed in Medellin in Colombia for a couple of months. Enough to know that that is a nice place to settle. There are some lingering crime problems, but nowhere as bad as the Escobar days. Probably as safe as Chicago. The ex-pat neighbourhoods (like El Poblado) are very peaceful and have a good standard of living. And the weather is perfect all year round.
Guayaquil in Ecuador blew us away by how affluent the country is compared to all of their neighbours. It's relatively clean and low crime, and the weather is great all year round, since it's right on the equator.
The only thing we don't take in account right now is healthcare. We're relatively young so it's not important to us, but if we were older we'd have to evaluate access to hospitals and doctors, as well as cost and the quality. And we have free healthcare if we move back to Canada.
So no place is perfect. It's always going to be a balance with cost and comfort.