So here is where the rubber hits the road. Due to the Gov't allowing the changes to Rule 41 in the Federal Rules of Criminal Procedure, the
FBI can legally install malware on your computer if it thinks you might be doing any illegal activity on your computer. They do need a warrant but now they can get a warrant from any Judge in the country instead of a local judge - and the warrant could be a blanket list of IP's that a Judge in Hicksville, AL may just say better safe then sorry. I have no idea what mechanism they have in place to let you know they have a warrant out on your IP.
Since the FBI cannot see the data in your Tor or VPN connection and sees you using these services they may assume you are part of a Child Porn ring or something and get a warrant.
The Rule changed in December 2016.http://fortune.com/2016/11/30/rule-41/https://en.wikipedia.org/wiki/Rule_41
There really is no real secure way to browse or use the Internet in the US anymore. If the Gov't, etc wants to monitor you they easily can
You would have to use a known list of VPN services or Tor itself for this to be an issue - Point-to-Point encryption to your seed server is probably the best way to go.