It's a scale. If you fuck around using Chrome and/or no VPN, you are vulnerable to dragnet surveillance and an easy target.
If you use VPN and a non-Chrome browser, you're still pretty easy to target via device fingerprinting - and most of the extensions to prevent this don't really work that well.
If you use VPN and Tor or i2p, you are a hell of a lot harder to target. Unless there's a state actor doing traffic analysis to match communication between you and your VPN service and the exit node of the Tor network, you are pretty safe.
I've yet to use i2p or tails; my "threat" model is basically saying "nigger, jew, tranny" and that's about it. When things get really ugly then I'll seriously use them.
I've used tails from a USB drive. It works. I would use it if there was a way to have a persistent password manager. It might have that, not sure.
Yeah I think for really serious issues when communication is censored and surveilled even more than it is now, those options- or better, will be important to use.
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