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As an example of a PDF that cannot be converted without manual help is the recently free (now no longer free) book Infected. It has different fonts to specify certain characters speaking and no conversion will get that right. So you have to go through the PDF with the converted file and fix it up by hand.
But seriously, PDF can be a bitch to convert without broken paragraphs, joined paragraphs, run on words, and other anomalies.
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