Here is my Wizard’s basic strategy for Monopoly: Buy everything. Advanced players may make exceptions if the property won’t help you make a monopoly, block someone else, and has little value as a bargaining chip. Utilities can also be declined in a cash-poor situation. Trade as well as you can. This is where the skill comes in. Try to trade for the best set you can. Here is how I rank them, in general: Orange, Yellow, Light Blue, Dark Blue, Light Purple, Red, Green, Dark Purple. This will vary depending on circumstances. In a cash-poor game, favor the sets that are cheaper to develop, like the light blues. In a cash-rich game, go for the ones where there is more potential to spend money on, like the yellows or dark blues. Once you get a set, whether naturally or by trade, build up quickly. Try to get to three houses on each property as quickly as possible. The marginal return per house drops after three. Mortgage most of your other properties and spend your cash. You want to leave a little equity for small expenses. Not spending your money is like a soldier in battle not using his bullets. Oppose all the silly house rules. This especially goes for the money pot on Free Parking (I can’t stand that one!). If you are more skilled than your opponents, you want to minimize the randomness of the game. This question was raised and discussed in the forum of my companion site Wizard of Vegas.