I really do believe there are pixies that live inside the computer and move around the code while we're not looking. It's the only possible explanation.

I got into it a bit with ilyena_sylph up there, but there are basically a lot of usability "hot spots" -- things that we, who have been using the site for ages and ages, know full well how to operate, but someone new would have no idea. And they take one look at it and go screaming, and wind up on another service that does things better (I'm studying Tumblr pretty closely right now, for instance, since it's the new up-and-coming place that a lot of people are heading to.) So we need to improve usability enough and to modernize enough that people won't dismiss us straight out of hand, because a service can't live just by being geared towards people who are disaffected with LJ -- we need to be able to attract and retain new users from elsewhere.

Still, I totally believe that there are ways to modernize without destroying what makes DW special, and without annoying people to death!

"Pretty" URLs aren't implemented yet, but it's in Bugzilla, and I've been poking at it on and off and wondering if I have the skillz to accomplish it. (Right now, I don't think I do, but hey, I work best when I'm working just two steps out of my comfort zone.) We also have a bug open for "index pages", which will be sort of like a mega links list, where you can create a meta-page that links to a bunch of other entries, which would work quite nicely for what you're talking about with the chapters thingy -- I've been wanting that for a while!