Thoughts on my post -
perhaps presenting an inverted symlink tree for www and resources would solve it ?
e.g.
/www/myblog -> /www/instance/packages/lars-blogger/www
/resources/myblog -> /www/instance/packages/lars-blogger/resources
I think then, designers using their tools and selecting image refs from a directory structure won't get botched up...
If that works, it's feasible the package manager could create/destroy the symlinks when sitemap is used to mount packages.
This doesn't address subsites - I haven't used them so I don't know how they work.