Using WordPress makes me feel like that boy at the Type-In. I feel like the words are going right onto the paper. Sure, the metaphor is a little thin, but the point is that when writing with WordPress (or any CMS, really), the distance between what I’m typing and what I’m publishing is very short. The only thing closer is editing HTML directly on a live page, but that’s something only crazy people do. On the other hand, publishing a static site is like sending a document to a printer. I have to make sure everything is connected, that there’s paper in the machine, and then wait for the job to finish before seeing the output. If something needs editing, and something always needs editing, the whole process starts over.
I’ve never thought of it in these terms, but there is a nice immediacy and satisfaction to WordPress for this reason. (Though naturally one shouldn’t compose in their CMS in any case.)
I might submit that his issue is a deeper one about on which platform and where to publish though given that he’s got almost as many personal websites as I do social silos. The tougher part for him is making a decision where to publish and why in addition to all the overhead of maintaining so many sites. However, I’m not one to point fingers here since I’ve got enough sites of my own, so I know his affliction.