No, not everyone is guilty, in fact it would be impossible to figure out who is and who isn’t ‘guilty’.
What I want to know is whether or not a businessman with a state enforced monopoly (for instance) should be allowed to keep his fortune. Or will the future libertarian society resemble modern day Russia?
Who would have jurisdiction to make any of these impossible determinations? You say it would be impossible to figure out, then you ask if a libertarian society would make impossible determinations.
If these people didn’t earn their money in a legitimate way, then they stole it(or whatever word you want to use that doesn’t offend ‘right’ libertarians). I don’t think that thieves own what they steal - so part of (almost all?) the wealth of these political entrepreneurs isn’t really theirs.
Can any voluntary interaction with a coercive entity other than trying to stop its coercion be moral? Any voluntary interaction benefits both parties. Why would you want to benefit someone who doesn’t follow the NAP? If you follow the NAP, and do an action that benefits someone who doesn’t, then aren’t you contradicting yourself?
Why are you concerned with levels of guilt? Guilt is guilt, yes? Why assume Walmart is guilty due to eminent domain, but the customer who supports Walmart and makes them profitable may be less guilty?
These positions you take are terribly arbitrary, and mostly ridiculous. No one is coercing millions of people to shop at and support Walmart. They do so of their own free will. If Walmart is guilty, then I would say their clients and suppliers are guilty as well.
How much? I’ll leave that to the nurture over nature crowd to quantify.