Still though, given that I have had lifelong impressions of Tokyo as being the most expensive place to live anywhere, I was pretty gobsmacked when I started doing the math.
The decor is a little bit eclectic (though I love wall paper), and the lake view is indirect, but it's a quiet little corner just a few blocks from the magnificent mile: https://maps.google.com/maps?saddr=E+Chestnut+St+%26+N+Dewit.... Only $2,000 per month for a 2BR and 1,000 square feet.
Also: give up. You're obviously moving back here. You bring Chicago up more than I do! One- of- us. One- of- us.
Easy, right? Not so much.
You see, if you got an on-site job in Portland, you'd have a choice: Live out in the suburbs and commute in, or go Urban and pick up a loft in the Pearl District. You've got maybe a 20 mile radius to choose from. Head over to Zillow and you'll have things narrowed down in an hour or so.
Ok, instead, let's see what happens when your choice is limited by "Someplace on the planet."
I spent the better part of two years auditioning surf breaks in various 3rd world countries, after drawing from another 10 years of experience backpacking around the world and stopping for months at various climbing destinations, beaches, cities, etc. I knew enough to know that no place is perfect in all respects, and that each new place you visit will just add another tick box or two onto the list of "things my ideal location needs to have". You get to learn a lot about what your (and your family's) actual priorities are.
Granted, it's a bit of a first world problem to have. But it's definitely an issue, and not one that you immediately think about when you land a gig that lets you work from "anywhere".
There was a point, early in my guy-on-the-beach-with-a-laptop era where I would cut my bill rate in half while working from the beach with a laptop. Clients were happy about that, and it more than paid for beers and thatch huts. Then one time I tried not cutting my bill rate in half. Nobody but me seemed to notice. So now I don't do that anymore.
Neither should you. The work you're doing is exactly the same regardless of where you do it from. Charge accordingly.
Edit:spelling
This would include visa requirements, and those related to the viability of renting an apartment annually, as a foreigner.
Otherwise, it's just (pleasant) daydreaming. :)