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Technical Research for Story

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Hi -

I'm currently writing a detective series. It involves a group of people that set up a private viewing channel for videos and live transmissions. These could be accessed by certain high-paying clients to see things they really shouldn't be viewing. Since I know next to nothing about this subject, I'm trying to get some technical info on (a) the way this could be set-up and (2) what traces it would leave on someone's computer. After all, I do want them caught. Right now the detective has a copy of one of the participant's hard drive. So the question are:

1) Would the most common way to set this up be through VPN? And then use some type of proxy server?
2) The video/transmission would have to be encrypted would it not? Would this prevent someone else from seeing what was actually shown?
3) How would the detective find evidence of this being done? If this person was using an anonymizer, would that show up? What about passwords, payment, etc. ... would that show up? I'm assuming the person would have to be facilitating the running of one of these private viewing sessions for this to happen. Is this correct?
4) Could the person be using another virtual hard drive where this information was stored? Would the detective have to find the link to find traces of what was done?
5) Could the encryption be broken? Would that be reasonable? Could the detective actually view the video or bits of a video? Or would someone have to have gotten sloppy? If they got sloppy, how would they have done this? By not cleaning the hard drive?
6) If the person couldn't use a virtual hard drive, is there a dump site they could use to store this?

Since I don't know the technicalities involved, I want to write it in sweeping terms, but remain accurate. So right now, person A is part of a ring, a scum bag, and has been doing this. The detective has made a copy of person A's hard drive and is trying to find evidence of what he's been up to.

Any help would be appreciated.
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