After years of building this site with my own custom software, I've decided to switch to WordPress.
My previous system started with XHTML content transformed through various XSLT style sheets that produced summaries, an RSS feed, a Google sitemap, and a common appearance across all the pages. The whole process was driven by an Ant script, and required no server-side code except for a comments form. It worked pretty well except for a few things:
I thought I'd take a look at some actual blogging software to see what was available. I ran across an extensive comparison (though I can't remember where that was now) where the person doing the comparison decided on using WordPress. I had thought about trying to use a .NET application, since I'm trying hard to learn .NET deeply right now, but there was a telling comment about .Text (the only .NET blogging tool considered) in the comparison. The reviewer said something like, ".NET programmers are more excited about .NET than actual working software." While a sweeping generalization, I sense a bit of truth in there. Also, as a programmer, it is good to be exposed to lots of things, so a PHP application seemed good for technical diversification.
I created my own WordPress theme, both in order to preserve my site's look as well as to learn more about WordPress. Then I needed a way to migrate my content. I don't have a ton of articles, but certainly more than a manual approach would work for. I tried adding a couple of articles by hand, and quickly discovered that the WordPress editor treats all whitespace as significant, unlike HTML's text flowing regardless of line breaks.
My first attempt at an automatic import was to transform my content to WordPress' native export/import format. I abandoned that after a little while because it was based on RSS, but added a bunch of stuff that wasn't really relevant for my content. I realized that I might as well just do an RSS import, which was easier.
The significant whitespace characteristics I noticed in the editor carried over to imports as well, so my conversion program had to strip out all the non-significant linefeeds out. I also discovered that if there were XML namespace declarations where the importer didn't expect them, then it would think that there weren't any posts to import. It would just say, "All done! Have Fun!", which was kind of infuriating until I figured it out. I think I've heard someone say that blogging software is only as good as its import and export functions, and I almost gave up on WordPress at this point.
Once I got my content imported, I was happier about WordPress when I discovered Ryan McGeary's WP-Syntax Plugin. I had thought about doing something like that myself at some point. I did make one small tweak to the plugin, though. GeSHi's default syntax colorings were a bit too much for me, so I switched the GeSHi option over to use CSS styles for the highlighting, and chose fewer and more subtle colorings. I'm sure there are lots of other interesting plugins that I've yet to discover.
There have been some glitches (bug-like behavior), some manual work required even after my automatic import, and still some things to figure out, but I'm optimistic that WordPress will work out.