Hi,
I have developed image recognition software in java very similar to the one you need, but adding move. It will be possible for me do this project taking into account that it will reproduce in the jpg image as a group of lines and circles in the DXF file as shown in your example, that's mean, I am excluding round borders as curved or elliptical polygons they will be represented in the DXF file as lines or small lines interconnected, the software will be able to detect circles and will put the output as circles. It is very important the jpg quality, you state in the text that the photo will be taken from a 90 angle to the surface, I think the example photos are not in that position, the software will be as accurate as the image could be, for this proposal the camera has to be in zenith position, I mean, perpendicular to the plane. If you agree it will be a pleasure for me to develop this software with the quality it deserves. Thanks.