Q. Dear CMOS, Would you say “in the artist’s more than fifty-year career” or “in the artist’s more-than-fifty-year career”?

Q. Can you please add “wise” to the hyphenation table? I’m curious if you would use a hyphen in a sentence like “Accessibility-wise, my favorite city was Tokyo.”

Q. Our style guide states that “healthcare” must be treated as one word, but would this extend to varieties, such as mental healthcare? Merriam-Webster lists “mental health” as a separate noun, so I’m genuinely confused whether it should be “mental health care” or “mental healthcare.” Thank you!!

Q. You wouldn’t write “lineeditor,” so why “copyeditor”? Please help before my head explodes!

Q. Working on software that has an e-shop, I see a very different use of the word “checkout” vs. “check out.” Should it be “checkout now” or “check out now”?

Q. Does CMOS prefer “best seller” and “best-selling” per the dictionary spelling (over AP style of one word, no hyphen, for both)?

Q. I work at an arts organization that has two artistic directors. Should I refer to them as “co-artistic directors” or “artistic co-directors”?

Q. I can’t find any consensus on this: does “quarter century” require a hyphen? Merriam-Webster doesn’t even have the term in its dictionary! (The nerve.) It seems that other online dictionaries do (and they also have a hyphen with “half-century”), but I thought it was odd that I couldn’t find “quarter century” referred to as a noun in either CMOS or M-W. Thanks!

Q. I recently read an article about a con artist who was described as “running a fine wine scam.” The ambiguity—is it a fine scam with wine or a scam with fine wine?—is driving me to drink. Is it acceptable in this situation to write finewine as one word to resolve the ambiguity? Please uncork me a good answer.

Q. A colleague wants to use a hyphen in the phrase “Friday-afternoon lecture.” But isn’t this an overly rigid application of the phrasal adjective hyphenation rule in a case where it doesn’t apply? “Friday afternoon” is not a true phrasal adjective, but a temporal phrase. “Join me for Sunday morning brunch” is the same as saying, “Join me for brunch (on) Sunday morning.” Interested in your view on which is correct, and why.