The best way to get this achievement is to load up a local two player game with the "GO and Movement" house rules.
This way if you land on GO, you can select to move yourself to either Chance or Community Chest.
Of course only auction off properties cheaply, splitting them between pieces if this is your last achievement.
This adds slightly better odds for this achievement if you're unlucky like me.
I won this over c cards and games.
The card that takes you to GO and lets you collect $200 does not count. Also there are mixed reviews, some have said you can get exactly $100, but others had to get more. Either way, just keep doing it until the achievement unlocks.
It has been suggested that negative cards count towards the overall.