Possessives and Attributives

Q. I somewhat often find myself struggling to find a grammatical construct for adding information about a possessive, particularly where the additional information is nonsubstantive enough that I don’t want to dedicate an entire sentence to presenting it. An example is: “The school’s, which is across the street, bell rings at three o’clock.” I expect that the answer is to change my phrasing. If anyone can guide me out of this desperate quandary, I’m quite certain that it’s my heroes at the CMOS.

Q. How does one make the following names possessive (and all first names that end in “s”)? James, Iris.

Q. My editor keeps correcting my possessive. Which is correct? (One person owns the house but several people live there.) We went to the Kerr’s or We went to the Kerrs’ or We went to the Kerrs. I used the first one and she says it’s wrong. Thank you so much.

Q. My fourteen-year-old stepson claims that the newest version of Microsoft Word “corrects” the contraction “it’s” by removing the apostrophe. He also claims that they “looked it up” online and that the rule has been changed so that neither the contraction nor the possessive has an apostrophe. I explained to him that the contraction and possessive of “its” may be one of the most difficult rules for people to learn because many people want to believe there should be an apostrophe for the possessive form. Are you aware of a so-called change? I never trust software and I am trying to convince him that he should not trust it either. Thank you for your time.

Q. Which is correct: “so and so, four months pregnant” or “so and so, four months’ pregnant”?

Q. When using a pronoun to replace the first noun when two nouns show possession of one item, which case should the pronoun be? For example, in the sentence “I’m going to my uncle and aunt’s house,” “uncle” is not in the possessive case. So which case should the pronoun be? “I’m going to him and my aunt’s house”? “I’m going to he and my aunt’s house”? Or, “I’m going to his and my aunt’s house”? And, if the answer is “his,” how do you reconcile that the pronoun is not agreeing with the noun it replaces in gender, number, and case? And what is correct if the pronoun replaces the second noun? “Megan’s and his room”? Or “Megan and his room”?

Q. A friend of John or a friend of John’s? I’ve heard that both are correct. A friend tossed the famous ambiguity at me this way: “A student of Einstein.” Unless it’s Einstein’s, then it might be taken to mean a student who is working on Einstein.

Q. My husband owns a production company with his brother. The name of the company is Deep-Dish Pictures. The brothers would like to state on their video jacket that the film is: A PEPPERONI BROTHERS FILM. No one in the production company can agree if it should be: A PEPPERONI BROTHERS FILM, A PEPPERONI BROTHER’S FILM, or A PEPPERONI BROTHERS’ FILM. [Company and surname changed for this forum.] Please help!!!! Thanks!

Q. Which is correct? (a) He has 15 years’ experience designing software, or (b) He has 15 years experience designing software. I’ve seen it written both ways. I believe “years” needs an apostrophe. If he has 15 years of experience, that would translate to “15 years’ experience.” Right? Please help.

Q. Would the phrase “The Board of Trustees meeting” be considered an attributive noun? Or should possession be indicated with an apostrophe? Thank you for your assistance.