You may want to look into the work of Matt Terry (@mrterry) from SciPy 2013 and earlier. There are a number of tools he created, using what may now be outdated matplotlib interfaces but which could save you time. One of which is yoink (
https://github.com/mrterry/yoink), which is particularly good with rastered data behind a color map.
Using tools like Inkscape and/or the GIMP you should be able to crop any arbitrary figure out of a scanned paper/image and transform it so it's at least relatively rectilinear. Save that out as an image and these tools start to be useful - though there may be some customization left to go depending on what type of figure you're digitizing.
Josh