Organization isn't to make the reader's life easier. Making sense of what one reads is largely an introspective activity. No matter how well-organized it is, you the reader have to regurgitate into a form suitable for yourself before you can digest it. This is called active reading.
When was the last time you noticed a popular magazine or newspaper with entire pages of text?
True, but books do it all the time---as does Joel's essay, except for the gratuitous pull quote in the very section under discussion.
Je n'ai fait celle-ci plus longue que parce que je n'ai pas eu le loisir de la faire plus courte. -- Blaise Pascal, Lettres provinciales, letter 16, 1657. (I am sorry for the length of my letter, but I had not the time to write a short one.)
Paul, I agree it needs to attract, entertain, and hold the reader but feel the verbosity is laziness in editing rather than style.
My understanding is that PG spends weeks writing and editing his longer essays. The result is obviously much more solid and digestible, but I'd definitely trade some of that solidity for more quantity. That might be key the difference between a blogger and an essayist.
Seriously, is it necessary?