So my advice will be, folks, use technologies like Tor as much as possible (and I'm not talking about poorly designed Tor Browser (from the security POV)), but setups like this one if you really care about your privacy.
Problem with this is that it becomes an arms race that you will not win - once the communication channels are sufficiently difficult to tap (cf: Signal, Tor maybe..) even for metadata analysis, the spooks head towards the edges where the humans have to interact in plain text with their technology - you are being monitored by your own equipment because that kit is common and readily subverted. Here's the NSA's head of tailored access operations (chief hacker) to provide an idea of who you will be up against :)
If you really have a need for private communication, how about visiting a random pub, or taking a walk in the countryside, maybe a round of golf with that special person? If your communication MUST be remote/electronic, then you have a lot of work ahead to mitigate the risks in design, parts supply chain, assembly, distribution and operation of equipment (cf: Lorenz machines in WW2, Snowden details of modified Ethernet sockets, etc.).
Yeah, I got you and you're right. Tough everything depends on your threat model. For most of us, the common private communication channels will work. If you are targeted, well, that's another story - then you are f****d in most cases.
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