These are what we call the 'YMMV items.' Things that some people find in this work. We call them 'your mileage might vary' because not everyone sees these things in the same way. This starts discussions in the trope lists, a thing we don't want. Please use the discussion page if you'd like to discuss any of these items.
Fair for Its Day: Jean Webster was an early-20th century feminist, and it shows, particularly when Sallie talks about voting — which women could not do at the time that the two books were published.
"Funny Aneurysm" Moment: At one point, Judy mentions that she will be able to know if a war breaks between the United States and Japan.
Real Women Never Wear Dresses: The end of Daddy Long Legs has made "feminists" scream and screech because Judy marries Jervis, even when this happens only after the huge fight in which Judy rejects his proposal at first, and also after she makes it clear that, while she loves him, she's her own person and he cannot control her. For even more irony, Jean Webster was actually an advocate for women's education and suffrage.
Values Dissonance: A given considering the age of the novel - however, it is particularly noticeable at one point in the sequel when Sallie uses a pancake tuner to beat the hell out of a boy. Made worse by the fact that more people were concerned about Sallie's nerves than the boy's limp. To be fair, the boy had been torturing a mouse.
Ugly Cute: Harvestman is a giant fat arachnid with very little hair who is also utterly adorable.
The Woobie: Scapegrace has shades of this at times, with his extremely sad and depressing dreams, which indicate his childhood was not exactly nice and his family was dysfunctional and screwed up. Oh and he's probably having the same sickness his dad had, showing the same symptoms, so there's the possibility that his days are numbered. And really, Harvestman and Crane are pretty much his only friends, and even Crane thinks him to suspicious and creepy, such as the scene where he immediately thought Scapegrace to be the cause of his missing son. It's hard not to feel sorry for him.