Monopoly Streets

Before you start your game you will be asked to select a rule set. Press the "X" button on your controller to ender a mode that will allow you to build "house" rules. Pick whatever rules you want and then start up the game and complete it. The achievement will unlock at the end of the game.

Tried the other solutions posted on here by "CougarSlayer530", "paulsmid" and "Ev3rything I Am" but could just not get the achievement to pop (was boosting this with a friend) - cleared cache, made multiple selections in custom rules to no avail.

Finally we both restarted the game and selected cloud storage instead of the hard drive where our saved games were, as we did not have a saved game on cloud, so in essence it was a completely fresh save file - played one custom game (as other guides state, just press X on gamepad and create some custom rules - I only changed one, which was just deal all properties at the start, set the game for one reserved slot and closed the other two slots - then invited my friend from xbox live party) and once in the game my friend selected the bankrupt option at the end of his first go and the achievement popped for us both.

Hope this helps and if you vote negative please say why so that I can improve this solution thanks.

Difficulty: 1/5
Time Needed: 1/5
Not hard either host a game yourself or have a helper host a game but you/they must select custom rules in order for the achievement to unlock. If you want the game to end quickly either you are a helper just declare bankruptcy and the achievement will still unlock.

if the achievment doesn't pop up clear the system cache memory played 6 games didn't pop cleared the cache memory played 1 more game and it poped up