Imperialism is getting opposed by pretty many liberal democracies, figures it's not that popular if you're not an empire. Best example right now is Ukraine. You should talk to Lithuanians or Estonians sometime. If you can carve yourself out a municipality somewhere that's the democratic political background for a co-op or something the larger state is unlikely to bother you, and if they do, you can make a hell of a stink in the press. Just keep everything above board, cross your 't's and dot your 'i's and don't be a cult. At least in Europe, that is, wouldn't be too sure about the US. But Canada should work. US might work if you pretend to be fundie Christians, which just might be worth the trade-off.

Cybersyn was hubris. That's why I also mentioned complexity theory: Really, understanding what's possible in that area is pretty much impossible without working knowledge in theoretical computer science, physics itself is beholden to complexity theory you can't find a name in a telephone book in less than O(log n) time. It's also why chaos (as in chaos theory) is infeasible to analyse, another thing to read into. The reason I mentioned cybernetics is not because of Cybersyn, but because it ties everything together and provides a general, and utterly (as in mathematically) solid theory of systems as such. That also includes individuals and society, there's literally nothing it doesn't apply to. Further things to look up include the biopsychosocial model, as well as practopoiesis.