Hyphens, En Dashes, Em Dashes

Q. How should the following be hyphenated, if at all? Two and a half hours.

Q. I tend to let my ear be my guide—and usually that works—so I need some clarification to ensure I’m on the right track. Can you clarify that I am using my hyphens correctly? Facilitate a core-team workshop to discuss . . . Develop a future-state document . . . Conduct a future-state assessment . . . Identify change-management opportunities.

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?