I'm a web developer with 1-2 years experience at a top agency in Toronto, ON. My wife is a successful Customer Success Manager. We would like to live somewhere that's more than 10 degrees celsius or 50 degrees fahrenheit year round, that's safe, and has interesting careers in tech/startups. Ideally an active location as we're both into sports (tennis, golf, biking, hiking etc.). Ideas we've thought of are San Francisco/Bay Area, Tucson Arizona, Costa Rica (Remote work but internet sucks), were thinking Thailand until political issues anything else we should look at?
I live in Tucson when I'm not traveling. It's very cheap and very beautiful. There's a large community of triatheletes that live here for the abundance of bike and running trails as well as amazingly beautiful pools. Get me anytime if you want to know more. Hope this helps.
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 ;)