[Joel]

Illustrator and the other Adobe apps will only scale text in a shape when resizing using their palettes and not when manually resizing the shape with the mouse; Lineform uses modifier keys to do so (and modifier keys are scarce in OmniGraffle right now as they are used for things like object rotation, etc.).

We're thinking about making a setting in the Geometry Inspector or some similar spot so it would be a property of an object, this of course will take a good deal of usability testing going forward.