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Monopoly is a game of chance. No one expects to be able to win the game all the time. We all have our bad streaks. It is however, possible to increase your chances of winning the game by using certain strategies and tactics.
Firstly, know the odds. Not all properties are created equal. Some properties have a higher chance of being landed on than others. These are the orange properties, the red properties and the railroads, in that order. Try to trade to complete either the orange property set or the red property set (the colour groups next to the Free Parking space), and be prepared to trade more valuable properties for them.
One can't always manage to trade for these properties though, and in the event that you are unable to trade for orange and red properties, or find that you have to pay too high a price to trade for them, the next properties that you should try to trade for should be yellow. Next should be the light blue properties and the light purple properties. In the event that you are unable to make a trade that secures you any of the above colour groups, try to trade for the dark blue properties (the two properties just before the Go square). Green properties are expensive to develop and are not landed on often enough to be worth it. The dark purple properties, while cheap to develop, do not collect enough rent even when fully developed to be game-breaking, though control of them can be combined with other colour groups to gain a monopoly on houses. (More on this tactic later)
It is not advisable to spend all your money on developing your properties upon completing a property set. One should always try to keep enough cash on hand to survive having to pay a large rent without resorting to drastic measures like selling off the houses that one has already built. There are of course, exceptions to this rule. Rent for developed properties rise drastically starting from the third house. Thus, in some cases, putting yourself into a cash poor position to build that third house is a calculated risk.
Another exception to the rule is when you are trying to establish a monopoly on houses, or when one of your opponents is attempting to. There are a limited number of houses in the bank and once all of these are bought, players are unable to build any more houses until a player has sold theirs. This tactic is particularly useful for players who own properties that are cheap to develop, and can either be used to force opponents into cash poor situations, or used to outright deny opponents any chance to develop their properties further.
One should also note that it is actually to your advantage to make unfair trades with one opponent if the resulting trade allows you to get ahead of the rest of your opponents. For example, suppose there are four players in a game and no one owns a property set yet. Mathematically speaking, each of you have a 25% chance to win the game. Now suppose that early in the game, you are able to trade to complete the light purple property set with one player, but he will only allow it if you trade him an orange property which will allow him to complete his set. Should you trade?
The answer is yes. Assuming that the other two players are unable to secure a property set through trades between them, their chance of winning have been reduced to almost negligible. While the player with the orange property set has a greater chance of winning than you, you still have a chance to emerge the winner, and it's far higher than a 25% chance.
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