Presumably there was some sort of punishment for ordinary citizens trespassing, and it was much higher than one dollar. So this seems more like a common law way of formalizing state corruption rather than an actual equitable outcome.

Damages aren't limited to purely financial. That's a modern myth to disempower individuals in favor of commercial entities. Take for example, insurance compensation where if you simply pay a company to make something right, they'll come up with copious line items to justify customary costs. But if you DIY to have control over the end result, you'll end up getting screwed with your time being considered "free" rather than compensated at your hourly rate.

Loss of privacy is itself a damage, in the same way loss of limb is with no commensurate loss in earnings. You have a good point that someone who willingly hands over their information to Surveillance Valley has much less of a claim of harm. But surely if I take costly steps to preserve my privacy (eg spending several hours to setup a microg phone), then those steps demonstrate that privacy has value to me. That's to say nothing of the long tail of damages from surveillance databases being leaked to the wider public, or resulting in wrongful arrest or prosecution (both also not generally compensated these days, or per common law).

To me, accountability should look like criminal sanctions for government employees. Just as it's illegal for me to steal from a store, it's illegal for the government to violate my rights - the two should be similarly criminalized. There's leeway for actions carried out with a good faith belief of legality, but that defense vanishes the moment they form conspiracies to insulate themselves with secrecy rather than remaining open and directly accountable to the People.