I personally think his longish style is great. I like to be able to read an article for a good 20 minutes. I wish more bloggers wrote articles with as much depth and passion as Stevey.
Paul Graham's tight editing style is great too.. don't get me wrong. :)
Steve's stuff strikes me as a stream-of-consciousness, spellcheck and then post, type of style. Do the 3rd and 4th paragraphs about jocks really contribute anything to his point?
But I still do enjoy reading all the anecdotes and slightly off topic stuff. I think that if it was too polished it would lose its edge.
The raw/unedited nature of his writing is what I like about it.
Did you notice the title of the blog?
2. "Mes Révérends Pères, mes lettres n'avaient pas accoutumé de se suivre de si près, ni d'être si étendues. Le peu de temps que j'ai eu a été cause de l'un et de l'autre. Je n'ai fait celle-ci plus longue que parce que je n'ai pas eu le loisir de la faire plus courte."
Bribes: Petit Dictionnaire des Citations http://www.bribes.org/temps.htm
A loose translation of the above quote: "If I had more time, I would have written a shorter letter."
From 1. and 2. it follows: Succinctness takes more effort. Yegge took no effort. All other being equal a succinct text is preferable.
Imagine the reader shock to read that one!