Re: "Internet e-mail is not a secure medium..."
I think it's both a mixup and a shortcut.
- free webmail services are inherently insecure
- pretty much anyone with a reasonably big pipe and minimal tech gorm can harvest email content and / or draw a "connection map" (which is where the intel value lies).
But email content can be almost unbreakably secure (GPG / PGP for example). That's one of my pet peeves: "serious" institution adding disclaimers to every outgoing mail stating that there is no way to guarantee email integrity, so they won't take any responsibility if they send you misleading info -or even malware- by email. Yes, there are ways, you lying bastards, you're just too cheap to implement them (or worst, that's a preemptive get-out clause if they do send you nasties).
As for network masquerading, well, I won't rant on that again, but if you're serious about it there are easy and readily-available solutions. Which doesn't matter much: history proves that unencrypted channels are good enough for terrorists because the limiting factor here is not technological: the plods are so busy trawling the humongous databases for evidence that their girlfriend is cheating on them that they wont notice a terr'ist if he sticks a fist-sized piece of C4 in their ass. Blanket surveillance, as everything else, follows the rule: "too much data is worst than no data". TB/s is NOT a substitute for proper intel.