This site is currently rendered using ZenWeb on FreeBSD and is hosted on one of my FreeBSD servers, named "Greed". ZenWeb allows me to use simple text files for all of my work, and it renders HTML in a consistant format and generates a comprehensive sitemap.
Originally, this website was created on one of my Macintoshes using Frontier. I thought that it was a novel concept, akin to what I wanted, but was more difficult than it needed to be for what I wanted. I also found Dave Winer to be a complete asshole, so I dropped it. Then I started investigating a number of tools on both the mac and on UNIX, and didn't find too much that I liked.
What I wanted (and didn't realize at the time), was a static form of a WikiWikiWeb. So, using an HTML rendering library in Python called HTMLGen, I went about writing one. Very quickly I had something that worked like my mind worked and my website went from 20 or so pages to about 160. It is currently above 200 pages.
While Python is a whole lot better than Perl as an OO language, I find it to be a rather unintuitive language with a really cumbersome syntax. In 2000 at OOPSLA I ran into the ruby guys (actually the programatic programmer guys) and finally bought their book. I'd looked at it before, but there hadn't been any good books out at the time. Ruby is a wonderful language with strong OO and a good solid foundation. I decided to rewrite ZenWeb in Ruby. Now I have a much more flexible rendering system.
I have many more things planned for this website. First I want to finish up many of the things I have started over the past few years and get them cleaned up... Soon, I will launch many new things on sites like sourceforge and get a whole mess of things up and running.