Why the big concern about paying anonymously? You guys are clearly using VPNs for things I'm not.
The three things I use(d) a VPN for are both things of no interest to the NSA or any US government bit.
1) Accessing financial (and similar) services where I don't trust the local network operator, even with SSL (this is useful even in the US, at hotels/conferences, and
2) to access sites I didn't want visible to my past overly-snoopy employer (surprisingly, they didn't block VPNs), and
3) back when I was traveling outside the US regularly and for longer, to access US based streaming services (I've since seen a number of stories about Amazon/Hulu/Netflix blocking VPNs, so no idea if that's still useful.)
The first would all be subpoena-able by the government anyway. In theory the latter would be, although they wouldn't care. As for the middle, unless I worked for the government, they would be unlikely to care that I was visiting Monster/Indeed/Glassdoor/Hired or the occasional not-porn-but-potentially-NSFW site on company time.
