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"Boardwalk with a hotel? That's $2,000! It looks like you're going to have to mortgage everything..."
Yeah, we've all been there. If you're on the receiving end, it's one of the coolest moments in the game. If you're on the paying end, you're secretly plotting the death of whoever owns that wretched property. However, if you think that's the best way to win the game, you're welcome to play against me any time. Monopoly is not a game of just getting the most expensive property and milking everyone out of their cash - it' so much more.
Early game strategies:
Buy everything! If you land an un-owned property buy it! If you don't have the money for it, mortgage something. It's worth it because it A. Gives you a property to make money on and B. It keeps the other players from having it. It's especially critical to buy it if someone owns the other property(s) of that group because it keeps them from getting a monopoly allowing them to not only get double the rent, but keeps them from building houses and hotels before you do.
It's okay to buy railroads for the same reason as above. If you only have one, you're not exactly going to get a return on your investment, but it comes in handy for mortgaging purposes if you need a quick $100 - and should you actually get three (or FOUR!) of them, you'll collect quite often.
Avoid the utilities. They're a money pit that might pay nicely if someone you get both of them, but they're otherwise wasted money that you can use to develop your properties later - or money that you can use better properties in their immediate neighborhood.
Any time you earn money from rent and/or cards like Chance/Community Chest, set it aside for future developments. Don't touch it unless you absolutely have to. Call it a "development fund" if you like. More on this later.
Middle game strategies:
Get the Orange Properties (the names are different from country to country, but they're always the properties that are six, eight, and nine spaces away from jail. They're inexpensive to upgrade (it only takes $1,500 to put hotels on all three!), and people land on those properties more than any other colour group in the game. When people get out of jail, they tend to roll sevens which gets them to Community Chest, but should the roll one higher or lower, they'll be looking at paying you $950 (assuming you have a hotel). Make ridiculous trades to get these properties. It will pay off in the long run.
If you can get the Dark Blue properties (the last two before GO) good
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How to win at Monopoly
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