Seriously! Think about how we deal with Android/iPhone apps.
I go to Five Below or a Dollar Store and stock up on $2-$3 items that are kind of neat even venturing into the $5 range occasionally for "premium garbage" yet I get on the Google Play store and see a really awesome app that fills one of my needs but it's $2! How can someone charge $2 for THAT? They only spent a year working on it and it fits my need perfectly but $2 is too much!
It's really weird, for sure.
I think the hardest part with things like the New York Times is that a lot of us are getting our news from aggregators. I don't give a shit about the New York Times as a company nor any others. I read down through places like Hacker News and click links there. If, occasionally, it's a link to a NYT article, I read it (or don't.. I guess?) but otherwise, if any one of the news sites disappeared off of the face of the globe, I'd be no better or worse off.
Also, $8/mon is nothing when it's one news site but if each site begins charging, using a news aggregator is going to be a very expensive proposition...