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I want to use Graffle to mock up a series of pages or views. Not necessarily the actual widgets on the page -- more like UML depictions for units of functionality. A Big square for the page/view, smaller squares inside for components/widgets on the page and then maybe smaller shapes still nested inside that say app specific things like "pending", "complete", "toggle button" etc ....

Yes, I can already do that ...

But now I'd like to begin building this application ... so I need to associate tickets with each of my squares. I'd like to be able to click on an item and see, in another window, a list of things to do. Eventually, the list would include bugs, features and even general notes. I could hand this off to someone and they could click through and see all the things that needed to be done - and where exactly they needed to be done and how they affect the UI.

I own both graffle and outliner. A smooth interface into outliner would suffice for what I want to do - I can manage the outline/hierarchy of things to do manually .... but I need a way to view and check these things off as they directly relate to the entities and shapes I've created in Graffle. Graffle needs to drive it or things will get out of sync... it would be like trying to keep the docs in sync with the code ... ain't gonna happpen.

Eventually, would be nice to make the ticket list smart ... select a ticket and take me to the Graffle component. Tickets would eventually be organizable/filtered/sorted by milestones, assignees and priority, etc. But alas I get ahead of myself by several years.

Does this type of functionality exist? If not, I think a lot of developers would clamor for this type of feature set.