I've had background projects working on Web privacy measures since the Junkbuster days in the 1990s.
Pretty much any practical measures I've thought of, I think of (usually obvious) ways they can be countered, and assume it's only a matter of when that measure is on the adversary's radar and worth their time.
Junkbuster --- now that's a name that takes me back! MITM proxies for filtering were far more common back then, but the "security" industry managed to scare most people out of using one, ironically causing them to only remain on corporate networks. I still use Proxomitron for this purpose.
Pretty much any practical measures I've thought of, I think of (usually obvious) ways they can be countered, and assume it's only a matter of when that measure is on the adversary's radar and worth their time.