@Kalen_Buchanio What came to mind is a combination of utilizing custom fields to further aggregate information (especially with their ability to be in the middle pane or inside the task) and then coming up with Advanced Search Reports using any field needed and the custom fields that you save as Favorites on the users that need them.
Sounds like you need all the levels of Asana plus the ability to aggregate in reports and then bring them back together with Advanced Searches for your management and team reporting…
I think the custom fields open up a number of ideas for reporting such as in the this book:
This is its associated blog
Maybe some of his articles on “cascading” would help
A custom field of Green-Yellow-Red would help identify the “stucks” which I assume is the focus of your weekly status reports.