I've done Toronto Canada to USA to Mexico to Vancouver Canada back to USA back to Mexico back to Toronto Canada.
Freelancing all the way from motel to motel. 11 great years living in Mexico.
Freelanced before high speeds came along. 7-12 day trips from motel to motel were the worst!
Seems no one has answered you yet!
Orginally from Saskatchewan, Canada. Possibly born in the wrong country as I hate the cold weather with a passion.
2 years (Asia) - HQ in South Korea (Busan) - traveled to China, Japan, Thailand and all around while in the region.
3 years (Mexico) - HQ (Queretaro) - traveled most of Central Mexico
2 years (Mexico) - HQ (Cancun) - traveled mostly around the gulf area
Never really had a desire to work/live in USA.
Europe crossed my mind, but if you can keep your costs down while traveling, you can live anywhere. In some cases it was actually cheaper for me to work/live elsewhere while also enjoying my surroundings.
I only been in two counties. I started in the US and ended up in the Philippines. I been freelancing here since 1997. All the while trying not to melt!! I'll still be happy to agree with Grant in saying, I don't like the cold !!
But in both in countries, I still ended up meeting people from all over the world. It's really cool in the idea that I get to meet people from all over the world and I didn't have to go all the way out there just to do so. This works out nicely for me since I completely suck at traveling and don't like doing it !!
I also hate the cold and absolutely loved the weather in Mexico. I was lucky that we did not live in a coastal area where the heat and humidity can be so brutal.
We lived a mile high in the mountains just south of Guadalajara and it was the most amazing experience. My US trips were more passing through...and as quickly as possible...on the way to another country.
We have considered many places worldwide but with 2 dogs and a cat we were very restricted. By the time they all passed away we were back in Canada (for healthcare) and reaching an age where travel was becoming more difficult.
There are so many places in the world to live where the cost is living is much less than the US and Canada and without having to give up much in the way of things you're used to.
The internet has definitely made freelancing worldwide more easy and it's the perfect opportunity to live somewhere else and still make a living.