Joe Jennet is having a lot of the same types of issues with two posts today concerning it and I have to say I agree with his thoughts completely. I think the biggest issue for me was really the lack of responsiveness by Userland. Both lack of response to issues with Radio and lack of response to what was going on with the blogging world.
I think for some people, Radio is just fine. I think if you are someone who just wants to put up a blog and post things to it regularly and you don't care too much about how the whole thing looks, it is fine. It's also fine if you have a lot of time to figure out how it does everything, because the documentation just plain sucks (maybe it has gotten better now, but it wasn't that great when I was using it). I found the whole system of how templates work in Radio to be very cumbersome and hard to work with. Especially compared to Blogger and Movable Type.
My other big issue with Radio is that the program itself is really only half of the system. It's a blogging client with lots of very cool functionality that most users will never use half of. I always wished that Userland would have released some kind of plugin type package for Apache. They released the community stuff for Radio, but that would have required me buying another license for it and installing it on my G3 and making that my web server, which is not what I wanted to do. In the end, I don't know that I'd say Radio sucks, but I know that I don't think it is living up to its potential.
On the other hand, Movable Type was quite easy to set up and the technical support I've received from them is wonderful (I did donate $50 to get support and two update codes). There are definite things I think they can do to improve their initial setup (I do still need to send that feedback to them after all I've written here about it), but overall my experience has been much better than with Radio.