WordPress is a fantastic Blogging software and it does have some Podcasting support, but its just not setup by default to have all the support a Podcaster would want.
I searched around and found iPodCatter which is is a good start, for getting the iTunes support, but its just not a fully featured Podcasters pluggin.
I then found a VERY nice Flash mp3 player that I really liked.
With these two pluggins a a basis for me to learn how to write a pluggin for WordPress and for the core functionality I wanted, I created PodPress which is intended to be a full blown Podcasters Plugin for WordPress.
Get it, WordPress, PodPress? Heh, I crack myself up.
This plugin makes it super easy to manage a podcast within WordPress, and it handles all the iTunes settings and enclosure tag support (the build in support in WordPress is flaky) so this makes it solid.