Quote 1
"What does it all mean, judge?" Sandy asked, squinting at the pictures through his smeared glasses. "Angela looks like Westing's daughter, and Theo looks like his father, the man Violet Westing really wanted to marry." (15.69-70)
While we're probably supposed to think these resemblances mean something, the truth is, they don't. In another melodramatic mystery, Angela and Theo could be in danger based on this resemblance, or they could be fated to fall in love. But they aren't, and they don't.
History is kind of amended in that a Theodorakis descendant marries a Westing descendant, fulfilling Violet and George's doomed relationship, but that marriage isn't based on look-alikes—it's Turtle, not Angela, whom Theo marries. It's almost as though these familial resemblances are nothing more than coincidences—helpful coincidences that keep some of the heirs from figuring out the truth.
Quote 2
His face reddened around old scars as he rejected a folded five dollar bill. "No tips, judge, please, not after all you've done for the wife and me." The judge had given him the entire ten thousand dollars. (14.10)
The judge (like Theo) is almost too good to be true. She's the best tipper. Technically, this phrasing also makes her sound even more generous than she is. Each pair gets ten thousand to divide between themselves, and most of the other teams split it fifty/fifty. So the judge really only had $5,000 to give Sandy. It's still really generous, but it's actually about equal to Theo giving his share to his parents.
Quote 3
You're awfully hard on yourself, judge. And on him. Maybe Westing paid for your education 'cause you were smart and needy, and you did all the rest by yourself. (21.41)
Once we find out that Sandy's really Sam Westing, this line takes on a much deeper meaning. Judge Ford's upset that she owes Westing a debt for her education, and she's never going to pay it back. She worries that Westing helped her out so he'd have a judge on his payroll. It seems here like Sandy is just trying to calm her down. But as Westing, this could be the full and only reason why he helped the judge in the first place – because she was "smart and needy," and he had the means to help her. He gave her the opportunity, but she's giving him too much credit.