What is it like to play Monopoly competitively?: originally appeared on Quora: The best answer to any question. Ask a question, get a great answer. Learn from experts and access insider knowledge. You can follow Quora on Twitter, Facebook, and Google+.
Competitive Monopoly is certainly a different beast than the casual games you may have played with your siblings growing up. Once you begin competing at charity tournaments, it only seems natural to then have the desire to become US & World Monopoly Champion.
The majority of players who play the game competitively know the statistics of the game inside and out, such as the fact that Orange color group will statistically be landed on more often than any other color group, which also contributes to it having the best return of investment of any color group. There is even a strategy to your token choice, and players have to roll for the right to use a token if 2 or more players want to use it.
As far as personalities go, you'll see a full range. You certainly have your abrasive personalities that try to railroad you into giving them exactly what they want and cheer at top of their lungs when you owe them a $12 rent. However, these players are generally considered "poor sports" and develop reputations for being hard to play with, which then can cause them to have a more difficult time winning a tournament.
There are those who play very passive-agressively because they don't want to cause a conflict or draw a target on themselves. They'll propose trades to every player just to see who is interested in what, and then find the best point in the game to exploit that knowledge.
The most common professions I've encountered on the "pro" circuit are bankers, lawyers, teachers, and folks who work in real estate. This surprised me at first, but it makes sense because so much of what sets tournament Monopoly apart from home games is the level of interpersonal dynamics that is required to be consistently successful.
Within regions, you'll definitely find competitors who are friends and may even get together socially outside of the tournaments. There is a group in Southern California that has "debrief dinners" after every local charity tournament which they all play in, and that is pretty much every single tournament they can enter. Through my time filming Under the Boardwalk: The MONOPOLY Story, I've now become close with many of the SoCal group and have begun competing regularly.
During the game, folks will certainly exploit any connections they have to give themselves an advantage, and more often than not, players are able to leave the hostile feelings at the table when the game is done.
For someone interested in upping their own Monopoly game, I'd recommend starting by reading The Monopoly Companion by Phil Orbanes. It's the first Monopoly strategy guide that I read, and I still think it's the best.