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Iceland
No. That’s Greenland.
Vienna, Norway broadly, Slovenia, Japan broadly, Canada, Alpen region of Switzerland
Thailand. Friendly cheap great food great medical care.
Japan checks all those boxes. I’m on a trip around the world as a freelancer right now myself. Other decent options I have found: Mexico City, parts of Vietnam. The Philippines is beautiful, but the Wi-Fi and transportation is not there. And parts of the Philippines are pretty rough. The Galapagos Islands are beautiful, but obviously remote and the Wi-Fi is less than optimal. I’m on my way to Thailand in a few days so I will report back here if this thread is still active.
I spent some quality time in both Tokyo and in Kyoto. In Tokyo, I was in the Asakusa Neighbourhood. Well off the beaten path and a 20 minute walk to the nearest subway stops. But the neighborhood was so wonderful. I believe I paid somewhere around $40 a night for a two week short term rental. Which was pretty good. It was January though so not tourist season.
I did experience a language barrier in Japan. I would say one out of every five people speaks some English. But if you have Google Translate and you know some basic phrases like excuse me, hello, thank you, toilet, coffee, etc., You get by pretty easily. Really just smiling, speaking respectfully, and adhering to some of the lesser known social rules will help you immensely in Japan and just about anywhere else in the world.
In Mexico City I stayed in Roma Sud. Which is (maybe) obviously south of Roma Norte. Both of those neighborhoods are super safe and very cool and walkable. I can send you a Google maps document of the best taco places. Frankly, I never felt unsafe walking in any part of Mexico City, but then again I am 6 foot four 240 pounds.
Spain
Do your research and find what you like. Barcelona, Madrid and Mallorca/Ibiza will be more expensive than anywhere else. It is generally safe (no guns). Food is good everywhere, slower lifestyle and everyone is friendly
Argentina. You need your think of the time zone, as you don’t want to be on calls at 3 am
I’ll work mostly with the US, so the time zone should be ok. Are you recommending Buenos Aires or other areas?