In the current implementation (ImageBundle) you would need to have separate copies for each orientation & scale. That's a really nice thing that the Cappuccino implementation brings. The new ClientBundle implementation promises to, at least, have the compiler flip an image left-to-right when appropriate for a user's locale:

      @ImageOptions(flipRtl = true) 

...and there's another hint for images that are intended to be tiled:

      @ImageOptions(repeatStyle=RepeatStyle.Vertical)

There's no scaling yet, but the tiling annotation covers some of the cases where you might want scaling (such as the edges of a corner-rounded/drop-shadowed box of variable size).