Hyphens, En Dashes, Em Dashes

Q. My staff and I encountered a phrase and there’s a bit of debate as to how to hyphenate it: Wall Street darling-ready. Some believe an en dash should be inserted between Street and darling, followed by the hyphen between darling and ready. Others, however, feel the addition of the en dash would make the phrase even more difficult to interpret for readers. Thoughts?

Q. Is this a true phrasal adjective, in which case it should be hyphenated as shown, or should it not be hyphenated? “We offer innovative and technologically-advanced solutions.” There is a difference of opinions.

Q. “One man-one woman family.” I’m editing a work and this looks wrong, but I can’t say why. Should it be a dash instead of a hyphen?

Q. Is it necessary or preferred to hyphenate complex phrasal adjectives like “master-chef-turned-food-writer Anthony Bourdain describes the Tuscan countryside as . . .”? Or does CMS prefer “master chef turned food writer Anthony Bourdain describes the Tuscan countryside as . . .”? I am having a hard time seeing how anyone would misread the phrase without hyphens. Thanks for your help!

Q. Please settle an internal argument. Which punctuation is correct for the following title: “Transitioning to More-Rigorous Assessments” or “Transitioning to More Rigorous Assessments”?

Q. I’m taking a popular online copyediting course. One of my answers to a quiz was marked wrong because I failed to identify “early-warning system” as an instance of incorrect hyphen usage. According to the answer key, this is incorrect because adverbs ending in -ly should not be followed with hyphens. I think early is used as an adjective in this example and should therefore take a hyphen.

Q. Does hyphenation render a diaeresis redundant? Because it wrapped to another line, the word naïveté was rendered as na-ïveté. Should this appear in print as na-iveté?

Q. Do I treat “as and when required” with a suspended hyphen when adjectival? E.g.: “an as- and when-required basis.” Or join up: “an as-and-when-required basis.” Unfortunately, we’re stuck with transcribing substantially verbatim legislative debates.

Q. This is going to throw some people, but here goes: I’m almost fifty, British school system education. We were taught that when an already hyphenated word appears at the end of a line, the hyphen should carry over into the new line:

After they were away for so long, their house

-warming party was a wonderful surprise.

Since the project I’m working on is British grammar, and yet I deal only with US people, this is a new one on them. Any input?

Q. I have a question about the use of a hyphen in a compound modifier after a noun if a form of the verb “to be” is used. For example, “He is a well-known man” is hyphenated because the compound modifier comes before the noun. What about “The man is well known”? I’ve looked at various sources and they seem to contradict one another.