A Critique of OpenStreetMap
41latitude.com
41latitude.com
I'd say if suffers from too much focus on the code/data and could use some dedicated good designers. They might face a stubborn community though.
It is about freedom and open-source, you can help, I do (one step at a time).
edit: You have to be aware that some of the issues ARE data issues. At least some of the state highway labels are.