I wouldn't say Portland is as lenient as it once was about squatting. This town is blown up and has been for awhile. The city has been trying to crack down on, "zombie homes" for a couple of years. If you couple that with the winter weather and resources that are already spread thin here, I would say find a warmer spot to hunker down or a smaller city that doesn't have the traffic of Portland, Seattle, San Francisco, Los Angeles... Tacoma, especially the south side is empty and not a "fashionable" place to live and therefore might have a lot of good spots. I know Aberdeen does, but the resources and weather are garbage.
My real question is though, it seems like all your posts on stp are asking for advice. Which is cool, but why don't you just go do it? Find a place, scope it out, get in and fortify your little castle while you find like minded souls.