Couldn't you take a screen shot or use Windows "Snipping tool"
And then,
Is it not possible to draw on your print screen map, crop and then convert the image to 300+DPI on Photoshop?
I like the style that you are trying to create, however I do think you may need to feather the clippings of yourself more.
Also the black writing on the third image needs to be perhaps a lighter colour (white?)
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