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I did it with my old textbooks and reference books. I used pdfbeads to put the images together into a PDF file after first cleaning up the images (using unpaper). Many people use scantailor for this. It's pretty simple, except for the "bookmarks" that are essential for reference books. Those just take work typing in the headings and calculating the page offset for each.
Pages with photographic images also took more work. If you leave the whole page as grayscale, then the text doesn't show up very well on an E-Ink device. I ended up writing a program for selecting areas that should be left as grayscale, and binarizing everything else to make the text stand out better. That makes it easy to read and keeps the file size down.
I don't recommend using JPEG for text unless you keep the conversion quality high. If you drop the quality, the text gets a bit washed out.
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