This is the most important thing. Give Jason some money. You want to live in a world where people like Jason can make a living writing on the internet. The way to get that is to give him some money. Do that first.
Then you can come back here for some views. Which is that I disagree with this:
"There are undoubtedly new blogs starting, and many more happily spinning along in various niches, but they’re not really part of the cultural conversation anymore."
It's more that they're not part of a particular cultural conversation, a particular cultural conversation which lasted a few years and was mostly people blogging about blogging. That was great, it was enormously fun and invigorating and it has mostly gone. It's been replaced by people tweeting about tweeting.
But other cultural conversations are doing just dandy. Just today I found a brilliant bit of writing on a blog I'd never seen before. A tremendous pile of inside-comedy-writing jargon. That cultural conversation seems fine.