How can I get offset to do the common sense thing that everyone wants it to do???

I'd like to offset edges to the outside of a shape. When I use the edit mesh tools -> offset, it refuses to fill in the faces in between.

So I have to manually bridge faces every time I do an outset? That's rediculous!

Furthermore, the flatten tool doesn't work. I wanted the flatten tool to act like an outset, but blender decided not to offset with it randomly, even though I applied the scale.