Hyphens, En Dashes, Em Dashes

Q. I can’t find hyphen placement in ages, such as “fourteen-years old” in the Manual. And what about “years-old”? Is that correct?

Q. Is “official-rate increases” hyphenated as written?

Q. “We are more than ready to analyze plan design changes.” For clarity would you recommend inserting a hyphen between plan and design?

Q. Is it prework or pre-work (for work that is to be done before a meeting)?

Q. I am copyediting a parent resource website and this comes up a lot. How do I hyphenate “this class is for three- to four-year-olds”? Is that correct? I have seen it as: three-to-four year-olds.

Q. In a scholarly book about popular culture, the author has used several -esque word endings, usually hyphenated. According to CMOS instructions for the similar constructions of -wide, -like, and -borne, I would be inclined to remove the hyphen. But the result is unsavory. Also, in the case of open compounds, should the -esque ending acquire an en dash? See the following: Tarantinoesque, Skeeteresque, Gandalfesque, Billy Idolesque, Sid Vicious–like, John Paul–esque, The Parallax View–esque.

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”???

Q. Is it: early-fourth-century-AD amphora? What is proper way to handle early fourth century AD amphora?

Q. When does one use hyphenation to break words? I already looked at the Manual and still have some questions. I have heard that when the text has a jagged right edge no hyphens should occur and when text is justified it is allowed. What about magazines, leaflets, fliers, catalogs? Can one be more liberal in these and if so is there some guideline on this?

Q. I work for a travel company and we are trying to figure out the proper way to write “eight-night stay.” I feel the number should be spelled out with a hyphen, while other people feel “8 night” is correct. I’ve been trying to find an answer in the style guide, but no luck. Thanks for the help.