There is some selection bias, the people that are busy doing stuff, typically don't write blogs "How to live with 500$ in chiang mai".
to give you some perspective: i've been doing the "nomad thing" for 5 years, although I'm not actively travelling around much, and mostly based in an asian city. All my belongings fits into one suitcase and 2 duffel bags - 80% is clothes. I am earning above 100$/hour coding, typically as remote contractor with the occasional onsite visit, not simple CRUD-stuff, but interesting and challenging work. I usually do full-time contracting with one client exclusively for about 1 year. Two years ago I spent 3 months exclusively on open source work (that itself opened up very attractive work opportunities itself). My living cost is also pretty much the same as back in Europe, but I live a life in luxury here.
Most DNs eventually "settle" down, and stay in one place for a longer period (think months), and everyone seems to have their default city/place, where they often return to because of friends, they like the vibe etc.
What I found was the close friends you have at late 20ies, you won't lose them, when you go back and most probably you will go back at some point.
Re 1: There's quite a few digital nomad couples, or people who find their significant other. 2) Children not so. Re 3: These all exist, but it's not (yet) the majority.
Re: Horror Stories: I have not yet heard of something worthy the title of a horror story, and i am somewhat involved in the digital nomad community.
