"There's not a monotonically nondecreasing level of freedom, though."
Well, if we do nothing but maintain the current level of freedom, we're doing pretty well, historically speaking.
That said, I don't think we're on a downward slope at all -- that's just techno-nerd catastrophic thinking. The problem is that technology races forward and allows new forms of communication, our sense of entitlement increases, as does the power of anyone (governmental or private) to be intrusive. It's a constant battle against change itself, not necessarily against the surveillance state.
For example, the supreme court said that phone call metadata was collectable without a warrant in the 70s. The fact that Reddit just became aware of this fact is not a fundamental change in reality, or an example of things getting worse -- it's just an indication of how technology has changed this generation's expectations of what "privacy" means.
You can't deny that CALEA, PATRIOT, FAA, the NDAA, CIA's black site and gitmo programs, drone warfare, drone warfare against US citizens overseas, etc. weren't steps back.
While ssh replacing rsh, SSL-by-default, no crypto export restrictions for (almost all) commercial software, certain legal decisions (mainly in the 9th), etc. were steps forward. This is all independent of what reddit/hn people generally know about the situation.
"auto-updating" client software and the cloud have advantages and disadvantages at the same time.
"You can't deny that CALEA, PATRIOT, FAA, the NDAA, CIA's black site and gitmo programs, drone warfare, drone warfare against US citizens overseas, etc. weren't steps back."
I can't? Most of those things don't affect US citizens. Drone warfare arguably saves lives (you'd rather that we send soliders to do the same things?). The other things present vague, hypothetical risks (when they present risks at all), and tangible, quantifiable benefits.
Look, I'm not saying that I agree with everything that's in the Patriot Act, or that I think that the US government should have a blank check to bomb citizens via remote-controlled helicopter. But when you look at the actual risks to citizens, you find that they're pretty theoretical. The people who are objecting the loudest usually have the least reason to object (which is, ironically, part of the problem -- organizations like the ACLU have traditionally had a very tough time proving harms to citizens, and as a result, their lawsuits keep getting tossed).
But if you're going to push me to be the devil's advocate, I can quite comfortably go to the argument I made before: we don't have cars blowing up (or people walking into cafes with bombs strapped to their chests) in our cities on a regular basis, and we manage to achieve that level of safety without needing the intrusiveness of the security state of even a "reasonable", western democracy like Israel. Empirically, then, we're doing OK. A lot of the teeth-gnashing going on here is breathless exaggeration from people who have such peaceful lives that they have literally nothing better to worry about.
When did we ever have cars blowing up on a regular basis. I get your point about general life in America being OK, but that is only because many people turn a blind eye to the evils that our government is doing in our name that work against us in the longer view.
There are short-term benefits that you're talking about, but long-term costs that you seem to be ignoring as well.