After 20 years, they still are adapting to the 'new' platform. Look through their site with fresh eyes: If you were designing a news website (rather than moving a newspaper to this new platform), how many design, UI and functionality choices would you make differently? A quick start: * The separation of different forms of content: They don't really mix text with video, images and graphics, even though most web-native…
There's a point to be made about the separation of print and web, but you also should consider that text is much more easily saved than images/video/interactivity. The NY Times is a journalistic paper, and part of journalism is to create content that will be readable for generations later. If someone comes along 20 years from now and tries to read about an earthquake, are they going to be happier seeing a giant "video 404" or being able to read it?
> The font in their title...
While I doubt I'd launch a product with that font in my current design, there's not necessarily anything wrong with harkening back to a design scheme that over a century old. The NY Times logo and font associate journalism that's austere and unchanging, and for that I'd say they're serving their audience quite well.
>The discoverability of content...
I'm fairly certain you're not meant to complete the front page. It's not a bucket list of things you need to check off, it's to give you access to the news that's currently relevant. If you go to one of the subpages the content discoverability is much better.