I seems like it would be better if there were a expand/collapse method coupled with drag/drop to form an organizational function for pages.
It might look something like this
Top Level Page-
Child Page+
Child Page-
Grandchild Page
Child Page
Child Page+
Top Level Page
Top Level Page+
Top Level Page
Child Page
So, Pages with children have a little plus sign next to it when it's collapsed, and when it's expanded its children show up undreneath (indented) in the same format (with plus signs next to child pages that contain children of their own).
Then, you could expand only the Top Level pages you need, and drag/drop pages where you wanted them to go. You could also drag/drop top level pages around as well, nesting and reordering them the way you want them to appear.
Just a thought, but I think this would go a long way in pushing WP forward as a page-based CMS. Page management, as is, it painful.