I was just in Thailand working for 2 weeks and I wouldn't worry about political issues. There are a lot of amazing places for remote work there that would support an active lifestyle.

My experience in Costa Rica last year was also excellent. I worked for 2 weeks there and didn't have issues with internet. I was in a fairly remote area as well.

SF is super expensive, but probably the best place to be for a web developer if you can afford it. You will probably get weather that dips below 10 degrees in the winter though. Wth incessant rain to boot.

Check out www.nomadlist.com for rich info on the best places in the world to work.

My wife and I are looking to do the same - from Toronto as well. Looking forward to seeing some other answers!

LOL @ Columbus Ohio ;)