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First of all you absolutely have to listen to the talk called "The coming war over general purpose computing" by cory doctorow. It's a bit technical, but it's more or less exactly about this topic and very good.
It may sound a bit alien, but internet licenses can actually teach you a fair bit about freedom vs privacy. There's plenty discussion about the differences in freedoms in the MIT, GPL2, GPL3, and BSD licenses.
GPL's designer and /g/'s patron god, Richard Stallman, devotes his life trying to figure out how to make computing completely free. You may read up on his teachings if you want to see what the extreme side of freedom looks like.
If you want a deep dive about """privacy""" on (and off) the internet, listen to the talk "Privacy is dead, now they're taking anonymity" by Steven Rambam. It doesn't talk about freedom much, but it shows you exactly what happened to privacy.
