Dear Robby,
First, obviously, thank you for trying our software and for reaching out to CADDIT.
In a way, this has been
asked before Let's explain..
"
Portable Document Format" conversion will always be tricky, because the kind of hybrid container format that PDF uses fundamentally differs from data structures used in CAD. Lines and circles are VECTOR entitles, but images and handwriting are RASTER objects. So, while CAD necessarily uses vector math-based formats, PDF is basically a COS based typesetting language which evolved from the old Postscript digital printing format.
progeCAD includes a PDF to CAD converter which does reasonably well with converting vector entities (like geometry) from Adobe's Vector graphics API. Since
progeCAD's PDF import is not integrated with its picture graphics support, raster data such as an embedded image or handwriting needs to be treated separately. This basically summarizes the "why" part.
The "how" solution involves other tools, some of which are also included with progeCAD. For example you can use a free tool like Adobe reader and Paint to copy-paste any images or handwriting from the PDF into a graphics editor and save the file as a JPEG etc. Then use the RASTER-TO-VECTOR tool which also comes with progeCAD.
Here is a video of how that works:
https://www.youtube.com/watch?v=2VQkzAZn8YI
As stated, raster to vector conversion is always going to be tricky. Please let us know how you go with it..