Incidentally, I'm planning a mini-review of PyDS against Radio Userland in a while here, but here's one thing I've gotten to work in PyDS I could never get in Radio Userland (without doing unsupported hacking on the Weblog core): Posts without titles, that actually can modify the generated HTML instead of just sticking an empty string in the template.
As you can see, I like to put boxes around my titles, and in Radio Userland, an empty title results in an empty box. Yucky. So I always wrote a title, even if I had to stretch. I'm thinking this may have inhibited some of my more off-the-cuff comments... like this one.
I suppose it will be for you to judge whether this is a good thing or a bad thing.