> Always hit an entry guard through at least a VPN.
That's a horrible misconception. There is no added benefit to using Tor over a VPN. It only worsens the risk - you're essentially creating a permanent entry node with a money trail.
But then there's the risk from undisclosed vulnerabilities. In early 2014, CMU researchers deanonymized an unknown number of Tor users and onion sites using the "relay early" bug. The bug allowed relays to communicate covertly in the process of circuit establishment. So malicious relays run by CMU could identify each other, and cooperate to deanonymize circuits.
And then the FBI subpoenaed all their data. It took over at least one onion site (Playpen) and then pushed its NIT malware to perhaps hundreds of users. Who were then arrested and prosecuted.
So when did the Tor Project learn about the "relay early" bug? They claim that they didn't know, and didn't notice the suspicious relay activity, until after the CMU people went public. But how do we know? Indeed, from what I've seen of the FoIA production about the Tor Project, I'm not so confident that they don't cooperate with the FBI etc.
Heck, until recently the tor team used 80-bit truncated sha-1, 1024-bit rsa, and 128-bit AES for their traffic, not to mention that the tor browser ships with javascript enabled by default.
And then, using onion services, there are two three-relay circuits that meet at a rendezvous point. One picked by the onion, and the other by the user. So even deanonymizing one of those circuits would be insufficient.
But that's all theoretical. In practice, there are likely undisclosed vulnerabilities. Perhaps lots of them.
I do agree that the Tor browser standalone is rather a joke. Especially if it's in Windows. You at least want to be using Whonix. And if you really care, Whonix in Qubes.
No reason to think that they would not do that.
> And then, using onion services, there are two three-relay circuits that meet at a rendezvous point. One picked by the onion, and the other by the user. So even deanonymizing one of those circuits would be insufficient.
It would be sufficient to de-anonymise one of the parties.
> In practice, there are likely undisclosed vulnerabilities. Perhaps lots of them.
My point is that you do not need an undisclosed vulnerability to break tor if you have enough resources.
But will doing that be worth it to find someone like me? I doubt it. I'm just a hobbyist and writer.
You're trusting a bunch of stuff, in using Tor. There's no way to know what share of relays are malicious. Or how many undisclosed vulnerabilities are in active use. Or whether at least some Tor Project staff are failing to disclose malicious relays and vulnerabilities.
You just don't know.
That doesn't mean you avoid using Tor. Because, in theory, there are no better options. But it does mean that you use it carefully.
For example, always hit an entry guard through at least a VPN. Better, through nested VPN chains. And use firewall rules to prevent leaks. Not just Tor browser in Windows.