I could probably blackmail the grandparents into paying a kind of ransom so I don't leave the country for an extended period :)
My apologies if this is unsolicited and unwelcome advice, but have you considered supplementing your income by replicating Chris' efforts on a much more relaxed schedule and in your spare time? Blogging handsomely supplements my income, without much effort (or time) required on my part.
I see you don't post too often. Do you submit your articles to many sites like HN or do they mostly get picked up by your existing readership.
High-Quality Content + Good, Ethical Promotion + Proven Monetization strategies = $x,xxx per month.
I describe in detail the steps I take in my upcoming book on technical blogging. (Shameless plug: http://technicalblogging.com)
When I'm too busy to promote an article myself, my regular readers will usually do it for me organically. They are generally not as thorough as me, but they get the job done. :)
Right now I'm entirely focused on putting the best of my advice into the book.
I used to get variants of this comment all the time. "Pfft you people living in low-cost countries like Japan have things so easy..."
People always ask how I can manage to travel so much and live independently when my take-home pay is so low compared to a salaried developer. The answer is that just like everything in life, it's about priorities. One person might prioritize cable TV and an iPhone for $200/month, whereas I'd put that money to a plane ticket. Granted sometimes things like babies or health problems don't give you a choice, but for many people, it is a choice to be chained to desks job they hate.
In those countries, it was more than enough to live well above average. Taxes are naturally also much, much lower which have a large effect.
At the moment I'm back in Europe for a contract. 2000 USD while living here? After 50% tax, that's only enough to cover half my rent! Techies in low-cost countries really do have it easier, as they can price their products / services to an international level, while still having low local prices.
While I certainly don't live frugally I don't own a car and the money is merely for things like rent, food and such. I have a baby girl though and my wife is currently at home. When she starts working again the picture would certainly change.
TL/DR Not so easy to replicate if your cost of living is higher.