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Calibre isn't inserting paragraph breaks, it's removing them. PDF is all hard line breaks. There is a function which removes them, but it doesn't remove every type of break to avoid false positives. False negatives are slightly annoying while false positives can confuse the meaning of the text.
Line endings ending in a dash are already un-wrapped in my recollection of the code, I'm guessing the dash you're seeing is a different unicode character than the standard hyphen/dash. Open a bug with the file and it can get added. As you noted the single quote case can't be reliably unwrapped, so not much to be done there.
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