The structures of the game should never contradict the structures of the content. As you examine the content elements that you've listed and chunked and match them with game structures, jot down ideas that seem as though they should be a part of your game. Shortcuts Jumping Several Squares Marrying into money. Hiring someone instead of doing it yourself. Getting an early promotion.
Some choices lead to a chain of events that are more risky than others.
For example, deciding to invest in stocks versus putting your money in CD's. If one path is meant to be riskier than another, put more squares on it that require turning over a card that describes an undesirable event. Or more squares that might send the player back to square 1. To compensate for this enhanced risk, make the path shorter, or let it also contain more squares that lead to the opportunity for desirable things to happen. Suddenly the rules change.