For example, for the sentence ...
She said - 'That'll be all, Two-Fry.'
... I want the characters shown in grey below to be detected:
You can organize your word-boundary characters into two groups.
A regex that works with your example would be:
Now all that's left is to keep adding all non-word characters into those two groups until it fits all of your needs. So you might start adding symbols and more punctuation to those character classes.