Quote 1
Theo had begun reading the refrain and ended up singing. He shyly laughed off his foolishness.
"I guess it doesn't have anything to do with money or the will, just Uncle Sam's patriotism coming up again." (14.53)
Theo's both right and wrong here. The quotation from "America the Beautiful" is an important part of solving the clues that the will offers, but solving those clues isn't what leads to the answer, or the inheritance.
Quote 2
How come he didn't know that? Because no one ever wonders where a cleaning woman lives, that's why. But he wasn't like that, was he? (18.23)
Theo's conscience strikes again. In questioning the assumption that people don't think about where cleaning staff live, he implicates himself as one of those people. Even though he's become more and more conscientious about stuff like this, Theo still has to work through his preconceived notions and ideas about people, which are often based on their appearances. Here, he realizes he'd been judging Crow based on her class standing. Let's get uncomfortable for a second – before this moment in the text, did you ever stop to think about where Crow was living?