Here's one approach to solving the first problem: handling both "it's" and "will-o'-the-wisp":

        (                   # $2: a "word" consisting of one or more o
+f
            (?:
                [[:word:]]  #   a word character
            |               #   or hyphen, quote, or both
                            #     with word characters before and afte
+r
                (?<= [[:word:]] )
                (?: ' | - | '- | -' )
                (?= [[:word:]] )
            )+
        )

[download]

For the double-hyphen, the easy solution is to replace it with space before parsing. The harder solution is to disallow it within the [[:punct:]]*, something like:

  # any punctuation excluding "-"
  # or "-" that is neither preceded nor followed by itself
  (?: (?!-) [[:punct:]] | (?<!-) - (?!-) )*

[download]

With those two changes, I _think_ it passes all your test cases.

With a sufficiently recent perl, the experimental regex_sets feature should let you construct "any punctuation except hyphen" directly as a character class, which would be more efficient than /(?!-) [[:punct:]]/. I haven't yet worked out how to do that though - it's made harder by the special nature of '-' in character classes, doubly-special in char class arithmetic.

In reply to Re: Problem with a text-parsing regex by hv
in thread Problem with a text-parsing regex by ibm1620

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