I've had a hell of a time finding blogging software that suites my preferences but for now I've settled on IkiWiki as my software of choice. It's still a bit new and rough around the edges in a few places (especially look and feel) but it does the important things I care about really well.
I'm still experimenting with this site so it will probably be changing around quite a lot as I figure it out how best to utilize IkiWiki. :-)