1. Yes, it is. It just mean that the squares such as free parking, mayfair etc have been changed to the names given. 2. I'm not too sure about this, but Richard Halliburton was a famous adventurer, so I assume it's saying William O. Douglas acts similarly to him in some way. The bench I believe is a group of people within the court mentioned. So William is the person that acts most like Richard Halliburton within that group of people. She is 'baiting' him in this because she is leading him towards an answer she wants to hear. She is fairly certain she knows what he will answer so she ask so she can talk about that instead. In this case it seems to be the Tropic of Cancer. 3. A point of order is a legal term which very basically just means a topic, to raise in this context is basically just to say, and to deliberate is the same as discuss in depth. So it's saying that she, The First lady, chose a topic and then they talked about it in detail.

This is complicated, but I will give it a go: 1. Yes, it is in the context of the game. Almost all spaces on a Monopoly board have a residential street on them, and in the game you buy those streets and then put houses and/or hotels on them. In this case the names of the streets have been changed as a practical joke. 2. No, it's not Douglas' title. I'm not very familiar with the people described here, but a construction like 'William O. Douglas, the Richard Halliburton of...' is a way of comparing someone with another person, where the second person is usually more known. For example, if you want to talk about badminton with someone, and they don't know anything about badminton, you could say: "Lin Dan is the Roger Federer of badminton." The idea is that the other person now understands that Lin is equally good in badminton as Federer is in tennis. As for baiting, that's what people do when they are trying to get a reaction out of someone else (try to get them to bite), just as we put bait on fishhooks to try to get fish to bite. So, she wants him to respond, or to become annoyed. 3. This one is not worth worrying about too much, it's very formal and quite hard to understand. I would say that 'raised a point of order' is just another way of saying 'suggested,' and that the 'politely deliberated' means that the Court is not really interested but discussed/deliberated the idea just to be polite.