Pragmatically, security needs to match the circumstances in order to get a fair balance between usability and security. For most people, hiding inside the noise is "good enough". However the issue arises if any one person gets the limelight thrust upon them for whatever reason. And we've seen examples of this with the phone hacking scandals in the UK and how some journalists also search social media accounts of previously unknown individuals who might hit the headlines. In situations like this, you can no longer hide your signal amongst the noise of the internet as you're not being specifically targeted.
So I guess the point I'm trying to make is the signaling argument only works because the odds are in your favour. But like with any game of chance, there's always the slim chance that you might be unlucky.
At least with stronger levels of security, your comms might be more visible in some circumstances, but at least very little can be ascertained from those comms. Generally speaking of course. However going back to your VPN vs Tor argument specifically, I do agree with you that the security benefits of Tor are largely overstated, so it's not something I use personally myself either.
[1] https://en.wikipedia.org/wiki/Security_through_obscurity
> in order to get a fair balance between usability and
> security. For most people, hiding inside the noise is
> "good enough".
I'd say it is different. This "herd security" business only matters if your adversary is the NSA. In which case you will need a complex security strategy that goes way beyond just picking OS.
If on the other hand you just want devices that behave reasonably, then you should select your devices based on their behaviour.
In the same vein, a device that's meant purely for TOPSECKRITDATA?! and has a small install base feels like a much bigger target as I'm signalling I have something I am explicitly trying to hide.
Yeah, I probably didn't express this very well. But I do trust Apple to take it seriously, and I don't think I could take seriously the idea of running an Android device these days from a security and privacy perspective, which is sad.