I agree that small leaks sink big ships. The situation is much different from that though, because in this case your ship is actively being shot at.
However, I don't agree that it's an unacceptable risk, and I outlined risk mitigation in my post. If you do all that, you don't have anything to worry about for the time being.
>do you want multiple computers
That's just the simple way to do it. I personally use virtual machines to handle that side of it, and my hobby VM only touches the internet via a VPN so no worries there. This is outside of the technical abilities of most people, so I'm not recommending it. I'm happy to help people set it up, but that business is best left to PM.
>new tricks
Most of the current development is focusing on site side scripting, so running a good adblocker (ublock origin is my go-to) will take care of most of it. Outside of that, they're developing some pretty smart heuristics algorithms that could potentially connect you to your alter-ego, but currently they're used for finding people similar to you in order to show you ads. You have to remember that showing you ads doesn't mean identifying who you are.
>Tenticles
This is just the thing. Eventually they'll be able to figure out if you're seeing escorts, or likely to see escorts, from your normal online patterns. They don't need social media to do so because everything you do online is tracked. Combine that with TER using google analytics (they do) and the dots aren't hard to connect and if you're reading this, well, google knows you're here.
What I'd like to point out from all of this are these three things:
1) It's too late if you want 'real' privacy.
2) They (whoever "they" is) don't really care that you're seeing escorts
3) They won't care until you're careless/clueless enough to become the new 'low hanging fruit'