The New York Times
I was intrigued when The New York Times started their paywall. I thought the price was high, but I figured "well, I'll cross that bridge when I come to it." It's been almost two full months since they launched it and the thing is–I've never triggered it.
I am a diligent consumer of news, including of The New York Times. I thought.
Mostly I read their stories via Facebook, Twitter, and Google Reader. And I read it on a variety of different browsers. Not only an iPhone or iPad browser, but the browser inside the Reeder on both devices, the iPhone Twitter browser, etc. In short, even though I'm logged in on my computer, as far as The New York Times is concerned, I'm at least five different unique readers. And thus, I don't trigger their paywall. So I still haven't paid for the New York Times digitally.
I recently also tried out a little pay-for-digital news with The Atlantic magazine app on my iPad. I had missed the last issue as I was in between subscriptions, and I thought, what the heck, I should read it this way. I paid the cover price, which I was ok with, but then the experience was terrible. The app crashed at least 10 times and finally I gave up trying to read it that way.
The best paying for digital content I've experienced recently was with the Kindle. Not just downloading books, but a Kindle short. $0.99 got me an interesting story about Apple from Forbes. It was easy to download, well-priced, and an enjoyable way to read a long article. And yet when I tried getting The New York Times and the New Yorker on my Kindle, I thought the experience was lacking. But for an individual article, great.