This isn't really a "what's the best program to" question, but more of a "what's the best network design approach" type of question.
Be warned, this will be fairly long.
Problem: In an age where gov't and corporate monitoring of our activities is routine, and where it is increasingly common for lawyers and courts to grab our online data to be used in such mundane/routine things as divorce cases, I shudder when thinking of the future. Mentally fast forwarding 10 years or so paints a scary picture.
Call me a slippery slope nut, but I see our online activities becoming more and more accessible in future years. Though I'm not doing anything illegal, I don't want some future bitter wife or some gov't or private investigator knowing every site I visit while online.