Don't be rich, Live rich

Always, always, always, always, always check visa requirements. If you need one and don't have one, you will be buying a very expensive plane ticket when you get turned back at the border. Default tourist visas for American citizens is 3-6 months most places, but you always have to check. Don't trust any website that's not the official government, and call an embassy if you're at all unsure.

This lifestyle might be appealing for some very short period of life, under very specific circumstances. You have to be young to not worry about health insurance. You have to have the job that is simple enough to be outsourced and complicated enough to be at least reasonably paid. You have to not worry about "career" or "experience" (which are just different words for "future"). You have to be from the first-class country to take advantage of the visa requirements with your passport. It is also interesting to note that things they can afford in certain countries, like going to the beach every day, would definitely be prohibited for them in their home country given their occupation (note their remark on costs in Argentina, which, I assume, are lower than in Belgium).

I can elaborate much further as few of my friends live this sort of lifestyle in South-East Asia. From what I know about it, it's definitely (a) not for me, (b) doesn't make me think that the future knowledge workers will work that way. I work on my own projects in one of the most expensive cities on the planet and it's hard for me to see how can I relocate anywhere without losing the advantages I'm getting from the infrastructure and population here.

UPDATE: Though seeing the world is awesome, I'd personally prefer saving 10-20K and taking a year off work for that.

Also, I could not agree more with the points about "working needs discipline." If you're staying in hostels, I would basically say forget it. I found it INCREDIBLY difficult to sit down and code when I was traveling around in hostels (like a tourist) and surrounded by fun people and things to do. In BA, I an apartment like the OP, which made getting work done a bit more tolerable (but still very challenging given the surroundings...)