The overall best strategy for winning at Monopoly is to do everything in your power to create monopolies and block your opponents from completing them. This means buying every property you land on initially and then using trades, sales and negotiation to get the best deals and build your real estate empire [source: Darling].
Serious Monopoly strategists also pay a lot of attention to probability and return on investment. The quickest way to make money in Monopoly is to create monopolies on the most trafficked parts of the board. According to computer calculations, several squares on the Monopoly board are landed on with far more frequency than others. The three properties in the orange color group, for example, are six, eight and nine spaces away from the Jail. This means that everybody who rolls their way out of jail has a relatively high probability of landing on an orange square. If you're able to build some houses or a hotel on those squares, you're going to get an excellent return on your investment.
Interestingly, those same computer calculations have figured out that hotels don't provide the best return on investment (i.e., they cost more than they earn over the span of the game). Instead, the best investment strategy is to build no more than three houses on each property in a monopoly since the rent increase from two to three houses is so steep [source: Collins].
According to the probability experts, the very best return on investment comes from buying all four railroad properties [source: Darling]. First of all, they're relatively cheap. And since there are four of them, there is a higher probability that an opponent will land on one and have to pay the $200 rent. One of the worst investments is a utility company. Even if you own both, the rent is 10 times the roll of the dice or a maximum of $120 or as little as $20.
Here's a tip about jail: In the beginning of the game, pay the $50 immediately to get out of jail so you can continue buying properties. Later in the game, try to linger as long as you can in jail, since moving around the board puts you at risk of landing on Boardwalk with a hotel -- which will set you back some $2,000 in rent.
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