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.
Fridge Brilliance: Giving Judge Ford clues that she interprets as offensive may actually have been a deliberate ploy to keep her from having her clues researched by outside agents, the way she'd had the heirs and Westing investigated. Because their content had racist overtones, hiring someone else (probably someone white) to track down possible meanings for SKIES AM SHINING BROTHER would've been terribly embarrassing for both parties.
Aspiring writer/chessplayer and dutiful son Theo Theodorakis, whose primary duties are to his parents' business and his ill younger brother. His infatuation with Angela goes unrequited, and he later becomes a suspect in the Westing House bombings after accidentally blowing up his high school chemistry lab. The fact he becomes a well-respected reporter, a published (if not particularly successful) author, and marries the now-hot-and-soon-to-be millionaire Turtle takes some sting out of it.
Angela could also fit. She spends the book dealing with her mother making a huge fuss out of the upcoming wedding, which Angela doesn't even want to do. She doesn't seem to have many friends and her bridal shower is full of women she doesn't even know. And she feels she can't just call off the wedding because she doesn't want to hurt her fiance or let her mother down. Eventually, she is so stressed that she starts setting off bombs to try to let off steam. In the process, she accidentally injures her partner (who is possibly her first close friend) and blows up her own face to keep her sister from being caught in an explosion. Oh, and what she originally put down as her position in life? "None".
On the other side of the coin, Turtle has to deal with the fact that she is clearly her mother's Unfavorite.
Grace Windsor Wexler herself has Woobie tendencies. A great deal of her unflattering, elitist, and prejudiced behavior is driven by the trauma of having been disowned by her parents for marrying a Jew — thus being brutally punished for the most open-minded thing she ever did.
Sun Lin Hoo. She spends the first part of the book completely homesick and unable to speak any English at all. It's implied that this is the case because no one speaks to her besides her husband. She becomes so desperate to return to China that she steals various items, but then feels incredibly scared and guilt-ridden over her actions.
Flora Baumbach becomes this late in the story, when it's revealed that her daughter whom Turtle'd envied had been mentally challenged, and her husband may have deserted them because of this.
Subverted with Chris, who would be a pitiable character if not that he's absolutely thrilled to be a part of something as exciting as the Westing Game, hence is too cheerful to be a Woobie.