The theme looks great!
1) This is a problem. Overall we need a way for resources of all types to live inside a theme. There should be a default theme that contains all the basic CSS, icons, etc that are needd for an install.
4 is also a problem. The theme is this caes is not just style, but also changing how certain pages work. That should not be included in a theme.
5-6 is a problem also. I would have thought all the custom applied css etc would have been removed for the Zen project, if not it definitely will have to be part of an effort to allow easy theming of OpenACS.