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Re:“PayPal has demanded that we monitor data traffic as well... by luispedrocoelho on Tuesday June 21, 2016 @06:35AM (#11944751)
Regulations will probably come in the form of making these types of checks mandatory.

See, for example, how US Senators pressure payment providers to check up on whether their customers may be profiting from illegal file-sharing:

https://www.leahy.senate.gov/press/judiciary-chair-leahy-urg...

If Dropbox-style hash checking of files could be seen as the standard in the industry, I can see how failing to do that could be seen by a court as potentially negligent.

Re:“PayPal has demanded that we monitor data traffic as well... by anonymousDan on Tuesday June 21, 2016 @11:21AM (#11946303)
Could be a good argument for client side encryption.