Rich,
The poor man's version can be simple. It is easy for the designer to produce a vector file the matches the image. He then sends the image to the printer and the vector file to the cutter or CNC router. The trick is aligning the 2. In the Summa vinyl cutters they use targets that are printed with the image. These targets can be printed at a position precisely located from zero so that a camera and software can deduce the location of the vector cut path around the image, from the location of the targets . I am not a programer and I don't know how to make camera identify a target, but it seems simple.