Hi Sean,
Depending on what you understand by development context and selecting presentations based on the development context there is already a solution in the image that can filter presentations based on annotations and method signatures.
GTInspector can be customized with a presentationFilter. This is an instance of GTInspectorPresentationFilter, and it is used by the inspector to filter views. For examples you can look on the class side of GTInspectorMethodListFilter and GTInspectorTagFilter. (Spotter also has similar support for filtering available searches.) This is described more in Section 3 in [1].
For changing dynamically the tags (annotations) that are in the context you can use the 'Filter presentations' option from the window menu of the inspector window.
The previous two filters are just two possible examples. Another possibility could be to automatically infer the context, but that's a bit more tricky. For that there isn't any timeline. However, we are slowly adding support for recording user actions in all GTools + ways to adapt the tools based on those actions.
Does this answer your question or you had something else in mind?
Cheers,
Andrei