A family member just wrote his PhD thesis. This is the toolchain he used to attach a legend to his statistical graphs:
SPSS outputs the Graph. He makes a screenshot, imports that into Powerpoint, manually builds the legend, takes a screenshot, crops this to only contain the graph+legend, imports that to Word, prints it as a PDF and then imports that PDF in his main document.
Predictably he got in trouble when he needed to change a label on every graph. His solution was "interesting": insert textboxes in the main Word document, align them so they are over the images so you can only see the label in the textbox as it lies over the image. Luckily, Word anchors the textboxes relative to the image, so when the images move about the page, the textboxes-plastered-over-the-wrong-label are moved correctly.
Needless to say, all references are hardcoded into the text (e.g. "see figure 3.14"). At least he autogenerates the TOC.
Maybe this is an instance of the Word-is-not-a-typewriter antipattern?