Finally figured out what was stopping Pointy’s rig from behaving with the Mesh Deform modifier. If the mesh that’s getting deformed has other deformations being applied before the Mesh Deform (like an Armature layer or shape keys), the Dynamic checkbox ticked before hitting the Bind button. That way Blender knows to account for the deformations.
So yes, here’s Pointy having a turn now that I’ve got that fixed. Silly Pointy. All I have to do is hook up some controls for these shape keys and the rig should be ready for some animatics. 🙂