Please allow nested Initiatives, Features, and Requirements to inherit and display any attachments that were added 'upstream'. Oftentimes it will make more sense to attach documents like wireframes and GUI designs, data dictionaries, etc. to a 'parent' entity so that you don't have to attach copies of it to multiple features. I don't usually have a separate document for each screen of the GUI design - it's more like a 20-page document that is useful for 10 different features. I don't want to hvae to add it 10 times.
I like the way AHA surfaces all the attachments on the "files" page, but then I lose the context and specific sub-set of documents.
As described in the comments, this can be achieved by creating and referencing notes which include any high level attachments which are relevant across many records. You can see more details here: using @ and # mentions within Aha!
At this time, because of the workaround noted, along with current priorities, we are unlikely to make additional changes in this area in the near term.