Via boing boing, a “surefire strategy” for winning a game of Monopoly by Tim Darling:
* Always buy Railroads; never buy Utilities (at full price)*
* For every other property type, only buy them to complete a monopoly or to prevent opponents from completing one. Often this may mean buying as many properties as you can early in the game, but watch your cash reserves.
* At the beginning of the game, focus on acquiring a complete C-G (Color Group) in Sides 1+2, even if it means trading away properties on Sides 2+3. After acquiring one of these C-Gs, build 3 houses as quickly as possible: no more houses, no less!
* Once your first C-G starts to generate some cash, focus on completing a C-G and building 3 houses in Sides 3+4.
* Note: 3 houses is the “sweet spot” in the game as shown in Table 1 below. That’s where you’re making the best use of your money.*
* Single properties are the least good investment if you don’t build on them.
* The only exception to the above rules are when you need to acquire stray properties to prevent your opponents from completing their C-Gs to accomplish the above strategy.