I have taught "The Cay" many times, and I found this to be many of the questions that I also had my students either research, or I provided the information for in order to establish background information.  The only question that doesn't help set the "historical context" for the book would be the one that asked about "Which 3 Major League Baseball players are from Willemstad?"  I think this would be a great questions for establishing a motivation to read the book, but not to establish the "historical context" of the book.

You're right about that one. When I created the questions I threw that one in there because we had several baseball players in the class. I work at a continuation school and some of the team had been kicked out of their high school and I was trying to draw those gentlemen into the lesson. They actually loved that question and one of them did an extra credit assignment on one of the players. Amazing how one question can make all the difference with some students.