Do all of this and you'll be fingerprinted as being in the fringe minority of privacy-craving web users, so for this effort to succeed, it might help for there to be some form of orchestration/automation and education to achieve all of these together with a wide population of people.

That'd be a startup or nonprofit project, not necessarily anything any of us can individually do and not stick out like a sore thumb unless somebody capitalizes on anti-privacy revelations which can galvanize the population in favor of self-education on privacy hygiene.

Paraphrasing (probably inaccurately) Bruce Schneier's answer to a question of mine on this topic at DEF CON: the best privacy solutions are the ones embraced by many people.