This is really nicely laid out. That statelessness and searchlessness in particular is a problem. It makes me think of Frank Chimero’s piece that looks at the character of the open web (edgelessness, essentially).
When we think about screenshots and other visual content there’s still this definition that depends on structure of apps and sites, and I’m not sure it’s the only way to think about it. Augmented reality, for example, could imagine a “screenshot” that eventually is dynamic and reflects what’s on a page or in the real world at a given moment.