I'm starting to see why our opinions are so different. You live in the US. I've never been there, but from what I've heard and what you wrote I see that you are living in an anarcho-capitalist hell, where "Eye for an eye", "justice", death sentence, utter respect for the Law and government, which cares about money more than its own citizens, is still in effect.
In contrary, in EU there is no such a thing as criminal trespassing! You can't just shoot people for this. In some countries (Finland, Norway, UK) land owners even HAVE TO let others onto their land for trekking, camping, etc. It is unthinkable for the government to take your land without your permission and even if it does, you can individually SUE ANY EU STATE and win. The first lawsuit against Poland was won by a prostitute... We don't have borders, cultural boundaries, everyone may live and work where they wish to. And the money is shared: e.g. I pay taxes in Poland, part of the money goes to the EU budget, then through EU donations to Finland wilderness management and they build cabins along the trail which I can then use for free. And there is unlimited free firewood as well.
So, Andrew, I don't feel any kind of psychological impact of trespassing when I'm out in the wild. Sorry if you actually felt upset by what I've written. My friend once had to break into a private cabin after having almost drowned under the ice. He warmed up, stayed for a few days, then left a note and some money on the table and had no further problems. My other friends once put up their tent on a green lane between two highways going opposite directions. Guess what? Noone cared. We have been also camping just outside Helsinki airport. It rained so we didn't have a fire, but, according to the law, we well could! Not to mention countless situations when I was offered help and even free $$ from absolute strangers.
And why not go 400km into the wild? Satellite internet and a friend rule out isolation. Even the most remote places on earth are within reach of a floatplane in some 3h at most, if you don't want to make the trip. Ridiculously dangerous, you'd say? Well, 2 days ago the chain in my bike snapped, and fell onto a road and I was pretty much ONE SECOND from death in a car accident. We should rethink what really IS dangerous... Civilization only offers an ILLUSION of protection, but we DO pay the price even if most of us can't see it.
But we all agree that having at least one, small, legal home on a private lot offers a lot of benefits. And this is not that expensive after all. I've seen offers that were less than $10K, for quite decently sized lots. I see though, that the argument: "No one can kick you out" is invalid in the US...