The Aim of "Web 3.0" - Capturing Human Context

Given that the aim of the Internet is to deliver information, or perhaps to deliver it with more ease than other sources, I have been wondering how it might be improved.

My conclusion is that the biggest informational challenge is no longer "What is the answer to my question?" but "What question should I ask to find something useful in [a given area]?"

This meta-question is not provided by traditional informational services (encyclopedias, search engines, etc.) because it contains a value judgment; information sources have no business telling you what to pursue or be interested in.
Instead by this role is traditionally filled by friends, family, communities, research tanks and even business competitors. Most of these entities now have varying degrees of presence online and yet many of my informational searches are first prompted by things I hear directly from other people.
Mostly want what we want is trusted expertise: deep knowledge, created through experience and backed by reputation. After all, if you knew one or more such people for a given topic, would you ever bother with an Internet search? Of course not!

We don’t really want a network of web pages, we want a network of people that have made their information available on web pages.

(The publishing of knowledge is key here because is makes the system scalable in a way that 1 to 1 conversations are not.)
Now consider the main problems of finding experts on the Internet: you don’t know who they are, you don’t know how deep their expertise is and you don’t know if you can trust them.
Each step has a cost of time and further reduces your final pool of experts that you will listen to. Each step also takes more time than the last, perhaps exponentially more, unless that meta-information about the search is shared with you by others. Trust is the most costly hurdle of all.
These steps are also true for off-line searches as well. In Economics they are called transaction costs: expenditures (usually of time) that must be made before any trade can be conducted. Since each trade by definition makes both parties better off, enabling more is better for everyone. The Internet is celebrated for reducing transaction costs, but I think it has a ways to go yet.