Hyphens, En Dashes, Em Dashes

Q. My understanding is that the word family is a noun or adjective. So if you use it in a sentence like “We ordered a family-sized pizza for the party,” is the hyphen used correctly in this instance despite the fact family ends in ly?

Q. I’ve read the sections on prefixes and on parentheses with other punctuation, and would be glad if you would weigh in on the following type of structure: (pre)defined or (pre-)defined; (sub)set or (sub-)set. I think it would be reasonable to rule that solid prefixes in parentheses remain solid, and hyphenated prefixes retain their hyphenation. I would generally explain such compact forms before proceeding to use them. Or, if they occur only occasionally, simply expand them. What do you think?

Q. We use postdoctoral as one word. Should we then also use postbaccalaureate as one word for consistency, even though spell check wants a hyphen or space? Both are being used as adjectives.

Q. When using an en dash to indicate a range of time, is it wrong to use from in front of the time range (from 9am–5pm)?

Q. When announcing a fundraising event, is it hyphenated or not? Stay at Home Tea or Stay-at-Home Tea?

Q. Dear CMS, I am nearly done revising my dissertation, but my advisor may not pass me on account of my lengthy em dashes! I am using Times New Roman, and apparently the em dashes are too long. Is the standard em dash in Times acceptable for thesis publication? If so, can I point my advisor to something in the CMS on this? (I am serious. I don’t think she would not pass me, but she has circled every em dash and said, “Too long. Fix!” on my drafts, and I’d like not to chance it.)

Q. I am editing a magazine article related to real estate and am struggling with how to hyphenate the descriptions. “With seven bedrooms, four full and two half bathrooms, this home has 6,000 square feet of living space.” Also, “This is a 2,000 square foot, fully renovated four bedroom, three and a half bathroom home.” What does CMOS suggest?

Q. If you are referring to a street address that includes two adjacent buildings, do you use an en dash or and between them? I’m working on a project that uses the following, and I’ve put in an en dash, but I’m wondering if and would be better: “the full interior renovation of 619–623 West 113th Street.”

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.