Monopoly Streets

Using 2 controllers, when you get to the screen that let's you select human or ai characters, select all human players (i think this is the default). Join/start with the two controllers. This will be a two player game. As soon as the controller that is not going for Quick Win can, declare bankruptcy. I did this in ~2minutes counting the load/unskippable nonsense, before i found the options to turn off the tutorial & move animations.


WoodlandSpirit graciously offered this video for inclusion in my solution. Thanks WoodlandSpirit!

Easiest way to get this is using Jackpot mode as you only have to double your starting money to win (as opposed to getting the other players to go bankrupt).
Buy every piece of property you land on and put a hotel on it straight away before you finish your turn. In Jackpot mode you don't have to own all the properties in that colour suite before you can build.
Most importantly, make sure you press B to fast foward whenever you get the option.
A little bit of luck is involved (or what the wife calls 'skill') as it took me a couple of goes. The wife did it first time - obviously!

Difficulty: 1/5
Time Needed: 1/5
This is a easy achievement. You can get a second controller and start up a game and after controller 2 goes have them declare bankruptcy. Or, you could find somebody to help you online (ranked or not ranked game) and after your helper goes have them declare bankruptcy. If this is done in under 20 minutes your achievement will pop.

I got this the non cheat way, but it takes playing a dork on line. EVERYTHING that he landed on he auctioned and I carefully forced him over the odds on everything and he happily paid over the odds and carried on putting EVERYTHING he landed on up for auction!

Finally he landed on Mayfair (the poshest one) and immediately zoomed up over 800 Monopoly Dollars. I happily let him do it as he had less than that in the bank. He won, the game bankrupted him and I got the achievement.

Cheers dork!