Hyphens, En Dashes, Em Dashes

Q. Do you hyphenate a proper noun + participle? For example, “the Delaware Department of Education-approved modules for Common Core”?

Q. Is it necessary to hyphenate “car-rental agency,” or is “car rental agency” clear enough? Also, the same question as it applies to “16th-century ornamental bridge.” Sometimes, I think writing has gone hyphen-crazy.

Q. I’m writing an email to academics, selling a product offered “24/7, 365-days a year.” Should I write “24-hours a day, 365-days a year”? (The word year appears at the end of my sentence.) I am stumped with the slashes (/) and the hyphens. Thank you for your time and help!

Q. Let’s say you have a phrasal adjective that includes an open or hyphenated compound, the word and, and an attributive noun, such as “sterling silver and diamond.” When placing this phrasal adjective before a noun (such as brooch), how would you use en dashes or hyphens? Would it be “sterling-silver–and-diamond brooch” or “sterling silver–and-diamond brooch” or something else? I would like to do “brooch of sterling silver and diamonds,” but that won’t fly with the fashion editors where I work.

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.)