Design me a Product

I want to convert jpeg files to CAD files. However, the CAD files will need specific measurements which are not in the jpeg files. Thus, whomever ends up doing this will need to spend some time sorting out the various measurements. The product will be jewelry, say 3 standard measurements per each jpeg. and there will be thousands of jpeg images that need conversion. The end product is jewelry in the form of bracelets, necklaces, earrings, belts, belt buckles and rings. each one of these will need three different sizes, which will become the Standard Sizes for each category...with an occasional larger or smaller option being ordered. There is a potential of somewhere in the order of 5,000 to 10,000 conversions, thousands of which can be done in batches as well. Three samples are attached. The job is to convert these files to CAD files with specific measurements; the measurements will be for women's jewelry, small, medium and large. Once the standard sizes are determined, virtually all of the jpegs can be converted using standard sizing. Of course, there will always be variables as well.