These visits represent the source of much of the book's drama. Each visit corresponds with a school-wide contest in which the visiting writer selects one student's work to be read aloud and published in the school's literary journal. Most important for the students, of course, is the fact that these legendary writers would be selecting them as the winner--in their minds paving the way for an inevitable life of literary fame. The Frost visit is humorous, as he selects a student's work that he believes is a clever parody of his own poetry. He accepts the piece as good-natured ribbing, even though the student's intention had been only to write something Frost would find beautiful.
Rand also selects a student's work in which she is able only to see herself. But the contest takes on a secondary importance, as Rand's speaking engagement destroys our protagonist's enjoyment of her work. Like many young scholars he reads The Fountainhead and becomes enthralled with Howard Roark's boldness and virtuosity. Then, in this case from Rand herself, he learns what the writer really had in mind and the idolatry quickly vanishes. I strongly recommend the Rand section for anyone who still clings to the misguided belief that her philosophy is worth a damn. Wolff's characterization of Rand is hilarious, and even if it is a little harsh I would say that it is fully deserved.
The climax of the tale coincides with the approach of Hemingway's visit. Some of the students pretend to dismiss Hemingway, but none of them are able to avoid ripping off his style. In an effort to channel Ernest's ability our aspiring writer takes up the practice of re-typing Hemingway's short stories. The strategy works, in a sense, but the outcome is not quite what the young lad had in mind--the fact that the story ends up being a little more like F. Scott than Ernest is the least of his concerns.
As for complaints, I shall now turn you over to Thomas Mallon of The Atlantic, who has captured my two central points quite crisply:
Old School's somewhat pedagogical nature inclines one toward a few schoolmasterish objections. Its gradual accrual (three episodes from it appeared in The New Yorker) may have lulled the author into writing a last chapter that, although a rattling good story, seems more like an appendage than a conclusion.... And let me say this, above all, Mr. Wolff: the lack of quotation marks around the dialogue is a ridiculous piece of postmodern pretentiousness that has no place in your book. Not when it can stand with the best of what some old boys (Louis Auchincloss, Richard Yates) have produced in a waning American genre.