Which writers require multiple readings, and why?

Reading further in Helen DeWitt's collection of 13 stories, Some Trick, and find her style to be dauntingly intelligent as well as off-putting. Story # 3 in the collection centers on a young man from Iowa whose ambition has been to live in NYC and be part of the art and culture scene. He succeeds, and is swept up in NY life because of his (Iowa-like) skills as a carpenter, plumber, appliance repair guy, and pest exterminator - one person after another brings him in to work on his/her apartment, in return for which he gets a piece of whatever valuable start-up the homeowner is putting together - it appears, by the end, that he is a wealthy NYer. This summary, I have to say, is far more clear and direct than anything in the story, which is full of arcana, particularly about programming, which is another "language" that HD "speaks." In essence, the story is condescending in a weird way: She seems to be mocking the protagonist's cultural eagerness and small-town naivete while also including name checks galore that allows we the readers to feel that we're the ones in the know: For ex., the protagonist has a list of movies that he declined to see until he moved to NYC, as watching these films in at the U of Iowa would be too out of sync w/ the spirit of the films - but of course the list of films reassures us readers that, yeah, we've seen all of these (if not, add them to our list!) so we're on the inside of this cultural bubble. The 4th story int he collection, about a Jewish intellectual asked to read from the OT as part of an Easter service - who takes offense as this invite for some reason. Honestly, I couldn't understand this story at all. HD, w/ her indirect style and he fascination w/ arcana, may require or merit multiple readings - or extremely careful and close reading at the first go. But why should this be so? Joyce, for example, among the most challenging of writers, rewards more than almost any other writer (Proust would be another one) on multiple readings - but there is also a clarity and beauty and insight easily accessible on first reading, esp in the short-story form. Sometimes difficulty or obscurity is the writer's defense against clarity and feeling.