Ask HN: Where to travel/freelance abroad?

Open ended discussion question! My girlfriend and I are SF based but looking to spend a few months traveling, starting around March. She's a writer/blogger/social media manager and I'm a freelance developer.

I'd love suggestions from the community for places to head to. Considerations are cost, safety/health, food, weather, interesting experiences, local dev community / ease of finding cafes to work out of. Would be fun to learn to surf/kiteboard while traveling. I figure that I'll aim for 2-3 days a week of client work to support us (which I already have). She'd like to pick up some work here and there as well. We'd like to see a few different places during our trip, but want to spend a few weeks in at least one of the locations. We're less interested in backpacking / changing locations nightly and more interested in the experiences of getting to live abroad.

I speak some Chinese and would love to return to there. She speaks some French. I also have family in Brazil. Current considerations:

Buenos Aires, Santiago, Shanghai, Tokyo, Chengdu

Look forward to hearing thoughts!

p.s. We've recently traveled to Japan, China, and Australia.