Hyphens, En Dashes, Em Dashes

Q. I am an American translator working in Germany and I am having difficulty determining whether the following formulation is correct according to Chicago style:

developing short-, medium-, and long-term steps for . . .

This looks so Germanized to my eyes, but perhaps I have simply been here too long. Thank you!

Q. In “University of California Berkeley,” for example, which mark would you place before “Berkeley”: hyphen, en dash, or comma? (I couldn’t find this in your manual.) My preference would be either the en dash or the comma, but never the hyphen. What say you?

Q. I’m wondering about the proper uses of the prefix auto-. When one cannot find the word using this prefix in the dictionary, is there a standard for how to use it? To hyphenate or not to hyphenate, that is the question. My specific example is autosequence, auto-sequence, or auto sequence. Which would Chicago recommend?

Q. Do you recommend using a hyphen when spelling out the time of day?

Q. Please help! My British colleagues keep giving me books to proofread (for US publication, so they should be in American style) in which phrases like “parent-teacher relationship” and “human-animal bond” contain an en dash rather than a hyphen. Chicago says that if either “parent” or “teacher” were an open compound (such as, I suppose, “math teacher”), an en dash would be appropriate—so am I to conclude that since this is not the case I should use a hyphen? As far as I can tell, none of the examples in the section on hyphenation pertain to this construction. Are the en dashes correct, or are they just British?

Q. The menu in our cafeteria shows that enchiladas are available “Tues.–Fri.” However, when I ordered one on a Wednesday, I was informed that enchiladas are available on Tuesday AND Friday, not Tuesday THROUGH Friday. When I informed the cafeteria manager that this was incorrect, she seemed shocked and refused to change the sign. Please help determine who is correct!

Q. Hi. I work for a county auditor’s office which publishes a voters’ guide for each general election and primary. Each candidate writes his or her own statement to the voters, as do supporters and opponents of ballot measures. In the interest of space and fairness, we limit the number of words each writer can use. Our recurring question: should we count a hyphenated word group (such as “32-year-old”) as one word or three? I’m in favor of counting such constructions as one word. What’s your vote? Thanks!

Q. My reputable dictionaries give “transpacific” and “transatlantic” but not “transindian.” On its own, “his transindian voyage” would probably be ambiguous, but if I were to write “his transpacific, transatlantic, and transindian voyages were remarkable feats,” there would appear to be little risk of ambiguity. Would you consider that acceptable? If not, how should I express such a thing?

Q. Are poets allowed poetic license to do practically anything with punctuation? I ask this in view of a poem by Emily Dickinson that seems to use the em dash in bewildering and inscrutable ways.

Q. I’ve tried to Look It Up, and I know other people are curious about this question, too—some of ’em can’t even sleep at night for worrying about it—so I’m writing you, O Mighty Editors, to ask where do the hyphens go in the phrase “two and a half times the price”???