I'm really curious why you think "it will be hard to make devices the chokepoint." Isn't that playing out, right now? What proportion of even freedom-aware people, especially outside the US, have a smartphone not controlled by Google or Apple?
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And fwiw (not much), re: my vague war comment, I am talking about the potential long term effect of complete societal value realignment. But, who knows.
I expect people to keep jailbreaking these devices because they want free music, movies and series. Especially if both Apple and Google further restrict side-loading, while simultaneously banning any torrent like app. If in addition the copyright industry continues to legally harras indiduval downloaders, that'll be good for anonymous VPN use.