It sounds like you might want a variation on the Schwarz-Christoffel mapping. This is a type of conformal mapping that can be used to warp a polygon to and from a simpler region, like a disk; although I have not implemented it, apparently it is computationally tractable.
For your application, you would set up a map from the original polygon to the simpler region, and compute the inverse map to the modified polygon; combining the two should give you a nice conformal mapping from the original to the modified polygon.
Conformal mappings are nice and smooth, but they can sometimes behave in unintuitive ways; I can imagine that an animated version might yield some entertaining "slidy" effects. The conformal mapping will preserve local angles in the interior of the polygon; this means that the size distortion very near a modified vertex can be severe.