Would it be too hard to add non TCP traffic tunneling? This already supports DNS traffic through the tunnel but I wonder it is feasible to tunnel all kinds of traffic (UDP and ICMP mostly) through it?
What Debian released is an stable distribution that is going to be maintained for the next 3 or 4 years. It is better to release something stable and well tested than bleeding edge stuff.
Many people don't get Debian. This is a released aimed for servers and stable workstations. If you want or need bleeding edge stuff you can use Debian testing/unstable or Ubuntu as you suggested.
The next release of Debian stable will have Python 2.6 as default and it is expected for the first weekend of February, so it is safe to start with Python 2.6 right now.
The funny thing to me about this article is I am already living in a country where you can live reasonably well with 500$/mo (I born and live in Venezuela). But you know what? This cheap third world country is a big piece of shit because of its political situation (Chavez).
So, from my point of view, I am just planning how to leave my country. But move to another third world country?? No way man... I would prefer to live in a expensive first world country and work as developer/codemonkey/entrepreneur/whatever.
So, if you choose to "retire" to a cheap third world country, check its political situation and background. Now, if you just don't care to be rescued by UN blue helmets when shit hits the fan, just be my guest...