This trophy requires you to land on a chance or community chest space and draw a card that results in you getting MORE than $100. There are only a few cards in the entire game that can do this, so this might be the last trophy you get.
Start a game with only two players (to increase the frequency of your turns) and choose the house rules that allow you to go to any square if you happen to land on Go. Whenever you land on Go, use it to move to either a chance or community chest.
Since the rolls and cards drawn are all luck based, there's little else you can do but cross your fingers and keep playing.