First off, play a 2 player game with the house rule, GO and Movement.
So I used a quitting out method to obtain this achievement. There's 2 good spots to be on the board and that's the purple and the yellow/green corner. From the purple, you have a chance to land on community chest AND chance. If you don't roll a number you need, just quit out and go back in and you'll be able to roll again. Once you land on either though, and you don't receive the right card, don't quit because I kept getting the same card.
The best spot to be is on the opposite side of the board. I liked being on the green properties (actually the community chest spot) and rolling from there. From the Community Chest, you can either roll 3 or 9 to land on one, along with 7 to land on Go. If you land on go, I would choose the Community Chest spot in the green properties and continue the method after that. I received $200 from a card and go the achievement. Proceeding to Go from a card will not net you the achievement.
Update: The to K4rn4ge as he gave me a good tip. If your playing with a 2nd controller, watch it closely and if it lands on a chance/chest and they receive $100 or more, quit out and then you'll know that card is next in the deck for you to grab.
Sashamorning says 'I suggest using 6 players at first. That will shuffle through the cards faster to get to a good one. Then have 4 players quit out, leaving just you and one other. Go through the rest of the guide after. Just my $0.02.'
NOTE: There is a chest/chance card that gives you $100. The firs time I got that card I did not get the achievement, the 2nd time I picked it up, it popped. Not for sure if there was a difference.