Also Katrina and Brom. Is she honestly flattered by Ichabod, or is she just playing with him, perhaps using him to make her other suitors jealous? And is Brom just a bully, or is he honestly in love and wants to protect her from a gold digger?
Brom Bones, seeing that he's the only one character in "Sleepy Hollow" who actually suffers some damages and injures. Not only that, despite his bully tendencies, his Establishing Character Moment and seeing how Ichabod only wanted to marry Katrina for money and free food, show that Brom Bones has some fairly good qualities that make you feel some sympathy for him.
The part where Toad, locked in his prison cell, silently cries blaming himself for the trouble he's got into it and vowing to never let his manias get the best of him again.
During the Halloween party, Brom sees the only other person who's not dancing is Tilda, the short chubby lady who usually follows after Ichabod. She's sitting by herself, clearly dejected that she doesn't have a dance partner, but looks hopeful when she sees Brom looking at her. Brom responds by cringing in disgust, and Tilda looks incredibly hurt.
Values Dissonance: The Ichabod storyline is more than a little sexist. Women are either manipulative teases or complete dolts. Even if this takes place in the 18th or 19th century...
Also, Toad and his friend toast "To the New Year!" with a pink beverage in cocktail glasses that is clearly liquor.
One student also draws a caricature of Ichabod Crane - and you can see him about to smack the student with a stick (only the sight of the student's overflowing lunch basket stops him). To a viewer who was born after the 1970s, this would seem surprising - though this was standard behaviour for teachers at the time. (Even when it was animated!)