This photo highlights the importance of board position when making a critical trade. Using my recently-completed Monopoly simulator, I’ve been able to precisely quantify the jump in win% when owning the light blues (versus oranges) and building when your opponent is on Mediterranean (the MOST DANGEROUS place for him/her to roll from) versus Connecticut (the SAFEST place).
The numbers along the bottom represent how much cash each player has before building, and the assumption is that both players build as aggressively as possible at the end of each of their turns…until one of them goes bankrupt.
All other property is mortgaged, to eliminate unwanted noise or variance.
My favorite is when starting with $1000 each. As the person ending up with the light blues, your probability of winning jumps from a miserable 32.51% to a favorable 57.7% just by timing it when your opponent is in solid striking distance!
The Monopoly Nerd's Blog! 
A common mistake is thinking you’re going to win the game with Boardwalk and Park Place. You’re better off getting a monopoly of the light blues or purples, because you can build houses and hotels sooner. Try and get to this as soon as you can, even if you have to mortgage other properties to buy the houses, it will pay off in the long run if you can build before your opponents. Also, the oranges and purples are good monopolies to own, since people are always coming out of jail and landing on those. The most commonly landed on properties are the reds, but the oranges are easier to build houses on. One cool trick, if you own a lot of houses, is to NOT upgrade to hotels. If all of the houses in the Monopoly set are out on the board, your opponents cannot buy houses to improve their properties. If you have enough houses on your properties, you could prevent someone else from buying them. If you go to jail at the start of the game, when there is a lot of unsold property, it’s worth paying the $50 fine to get out. But later on, when other players have houses or hotels, it’s worth staying in jail the whole 3 turns, during that time you’re not landing on other people’s hotels, but they could be landing on yours. Those are all the tricks I know – stay alert, pay attention to people landing on your property. Beyond that, it’s the luck of the dice as to what you land on to buy. Also, if there are any “House rules” about trading property, auctions, money on free parking, etc. be sure that everyone agrees on the rules BEFORE the game starts.
Thanks for your insights and comments on the game. While I disagree with you on some of your points (ie. saying that the reds are landed on more often than the oranges is not true), I appreciate the effort and accuracy of the majority of your statements.
I love your point about agreeing on house rules BEFORE the start of a game! This can save a LOT of time and heartache. 🙂
I agree, but I would’ve highlighted the word “just,” as in “It’s Not JUST A Game Of Luck.” Luck does play an important role in the game. Yes, much of what is called luck is just a set of probabilities one plans for, but for all the strategy in the game, there is also an element of luck.
This is also the way that I think of it, but the reason I’ve emphasized “not” is because most casual players conclude that “it’s all luck”. 🙂