Money quote in the last paragraph: "When we get into things like this," [Judge William Downing] said, "anonymizing stuff, that’s well over my head technologically, then it becomes very murky and hazy." That sounds to me like the judge likely wouldn't have known what a TOR node was if the police had told him these guys were running one. Technology isn't slowing down, so how can we make sure the law keeps up?
That depends on what you me by "the law". Paper based systems simply can't keep pace with the speed of information flow in electro-magnetic systems.