Hyphens, En Dashes, Em Dashes

Q. Hello, my question concerns hyphenating the term “anti-Second Amendment.” Wherever I see it, it is hyphenated as in my first sentence, but if the purpose of the hyphen is to let the reader know which of the words are linked, then “anti Second-Amendment” would seem to make more sense. But my spelling checker flags this alternate hyphenation. Is this an instance where we would be justified breaking the rule?

Q. How does one, using a word processor, make an em dash/en dash distinguishable from a hyphen?

Q. A recent article in Science magazine included the following sentence: “Every 10 weeks, Sundquist gets 32 bee sting-like injections of the nerve-numbing botulism toxin into her face and neck.” Should that be “bee-sting-like”?

Q. Dear wise and knowledgeable CMOS person, a fellow writer and editor and I can’t agree. She insists that “well-trained dog” shouldn’t have a hyphen. I think it must have that hyphen. We were both pretty tired when this cropped up, so we ended up barking a bit at each other. We’d like to resolve this bone of contention by appealing to you, whom we both respect and trust. Whatever you say, we’ll abide by.

Q. It seems that all types of dashes are treated without spaces in Chicago. Is the use of a hyphen with spaces ever acceptable (word - word)?

Q. I understand that adjectives modified by adverbs ending in -ly are always open. But what about instances such as “provide developmentally appropriate information”? My instinct is not to hyphenate, but I don’t think developmentally is an adverb here, so I’m not sure if the always-open rule applies.

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.