So I have been on so many different blogging platforms, it's not even funny. The last one I was using was some I wrote custom in Kohana. I was pretty happy with it. The only thing about it was that I never took the time to build a good admin for it. Since there was no good admin for it, I never took the time to update it manually.
I'm not a huge fan of WordPress because it is a resource hog, but it makes it easy for me to update my blog, which is what I want. If I happen to stumble across a large amount of time, I might write my own again, but I'll probably stick with this for now.
I'm really loving WordPress 2.7. It's really pretty. For the original move from my stuff, I just copied all of my old styles and such over. I need to add commenting to my template and possibly a sidebar at some point. As always, it's still a work in progress.