As I understand it, he was trying to avoid being subjected to a second frivolous, highly stress-inducing investigation based on people trying to persecute him for doing nothing wrong. Are you now telling me that it's a case of fraud to try to avoid drawing the attention of those seeking to persecute you for nothing more than performing perfectly legal actions? The fact the investigators in the first case were FBI agents doesn't absolve them of culpability for pursuing an improper witch hunt investigation -- and the fact such a witch hunt investigation could result from Aaron's perfectly legal actions might have been enough to give him pause, to rethink how he does things so that he might be better protected.
He probably figured "Well, this won't protect me from a targeted investigation, as it in no way really conceals the identity of the person doing it, but it might not trigger flags in some piece of software following network access behavior patterns on behalf of the witch hunt division of the FBI this time."
Everything before the last comma in that hypothetical quote says "This is not fraud. I am not pretending to be someone else." Everything after that last comma says "I'm afraid of how people will ruin my life for doing something perfectly legal, so I should try to mitigate the likelihood of that."
Yes, the technology is relevant, because the person using the technology in this case surely knows how it works and, as a result, surely is not using it to try to accomplish something (fraudulent concealment of identity) that he would know would not work anyway.
How do you get form "This totally doesn't work like that, and Aaron Swartz would know it!" to "Aaron Swartz must have been trying to use it like that!" anyway? That makes no sense. It's like trying to prosecute a greenhouse manager for allowing Japanese maples to be grown in his greenhouse because they look like marijuana to the layman. "Marijuana is illegal, and this looks like marijuana, so we should put people in jail for growing this even though it's not actually marijuana or illegal in any way to grow it -- even if he's growing it knowing it's not marijuana because he's an expert horticulturist."
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