The thing that sticks out the most to me in Andy's critique is how he skims over the fact that news sites currently have a lot of ads to keep them afloat, and r

The thing that sticks out the most to me in Andy's critique is how he skims over the fact that news sites currently have a lot of ads to keep them afloat, and removing them requires dismantling entire ads sales departments, marketing departments, industry standards for ad sizes that must be available on your site for advertisers to even want to talk to you, and the bottom line: huge chunks of money (especially for big homepage campaigns). This is something that every designer (and developer) at every media organization has to struggle with. And it speaks to what you said about someone looking in from the outside. It's very easy to create something like Andy's lovely design (and I'm sure every designer at every media organization has created or has wanted to create something similar), but it's another thing to design around all these ad sizes and push back on ad sales to have more room for creativity.