The problem is that most people already pay some digital subscriptions. Music 10 bucks, movies 10 bucks, and then a single newspaper wants 10 bucks per month. That's a bit much just for digital content. And you pay for the internet you're using right now, too.
As an Internet Service Provider I'd buy such subscriptions and offer them free to my customers. Maybe we'll see WP content free for Kindle users sooner or later, and other people would pay 10 bucks per month. I don't think that paywalls work for newspapers. It doesn't work if you get 24/7 TV entertainment for almost the same price.
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