Since I'm singled out as a source of Will's blogging ambivalence, I might as well offer my own thoughts on the matter.
I find Will's endorsement of Twitter exasperating. Will and I used to argue about his insistence on stressing that the "right" way of blogging was to write well thought out little critical essays. I felt this would tend to lead to people not blogging, and it just seemed unnecessary, since many, if not most, successful blogs have short informal posts. If you want to write quick posts, can't you do that as easily with WordPress? I'm not saying Twitter and blogging are exactly the same, but nobody is forcing you to write long blog posts.
Also, I've always configured my news reader to use the "river of news" style that Twitter encourages. I never read individual feeds out of sequence, and if I thought I could save a feed for reading tomorrow, I'd unsubscribe immediately. There are some feeds whose posts I skip over 80% of the time, but I keep around because I have some personal connection, but I never, never, never let anything pile up in the aggregator. So my reading experience has always been relatively Twitter-like.
Concerning Will's broader ennui, I don't think the traveling consultant/speaker role is healthy, and the fact that this role can be so influential in our business is a double curse. You have to be kind of crazy to want to do it, and doing it will only make you crazier, making the whole discourse less and less sane.
The fact of the matter is that Will has maxed out how far this online community can take him intellectually. He's gone as far as he can without embarking on serious scholarship of the kind that just doesn't take place on blogs. And by that I don't mean that serious scholars don't blog (although few do in this discipline), but in particular they don't blog about the foundations of their discipline. We blog about things that are current, not fundmental (unless they overlap). It is the nature of the medium.
Essentially, Will needs to go to graduate school. Unfortunately, graduate school sucks in general, and in particular, graduate schools of education overwhelmingly suck. So you'd need to find the right one. Also, he is too old to go to start a new graduate program. On the whole, this is useless advice. But it is what ought to be the next step. Alternately, one could make a list of 50 not very easy books to read on education and plow through them on one's own, but it is not really the same effect.
I am always amazed when teachers write about how much more they've learned from the online community than their teacher education program. I learned vastly more about teaching and learning in my year at Brown than I have reading blogs. There is really no comparison.