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Ok so the way that you play monopoly is:
Step A) Gather up as much property as possible.
Step B) Once most of the property is owned, make deals to gain monopolies.
Step 3) Win/Lose based on whose properties you land on.
Going to jail at the beginning of the game is very bad, you lose the opportunity to gather properties. Going to jail at the end of the game is very good, you don't have to chance landing on someone's monopoly.
The trading phase is the MOST IMPORTANT stage of this game. If you refuse to trade, or make bad trades, you can completely fuck the game. Not just for you, but for everyone else. Because you hold deeds that other people need to complete their monopolies. So if you give those away for a bad price, the person who gets them can walk away with the game. Or even worse, if you refuse to trade, those who DO trade and get monoplies will clean the rest of you out of the game.
Another important point:
Although the property's value is somewhat relate to its list-value on the card, when it comes to monoply-making trades, you have to consider more than just the paper value of the card. For example "if I give him a monopoly for this price, he'll still have all this money that he can use to build houses.....therefore I will only trade him this deed if he gives me an absurd amount of money, and thus won't be able to build properties right away". In other words, you need to think in terms of the winning the game, not the paper value listed on the card. It's entirely commonplace to trade properties for 5x, 10x their list-value, especially for monopoly-making trades. Giving someone a monopoly while they have a huge bank account to build it up is foolhardy, unless they're giving you the same opportunity.
Properties increase in value as you go around the board. The poorest are right after GO, the richest are right before GO. There are special cards that will send you to certain squares. For example "go to Boardwalk" card, that sends you directly onto the most expensive place on the board. Thus, although this monopoly only consists of 2 places, and thus people have a less chance of landing on it, it can still be a game-winner because of that card. I believe "Go to Marvin Gardens" is another one.
I think that in general, having more monopolies is better than having more expensive monopolies, because you have more threatening spaces on the board, and thus more consistent income.
There's also a bit of trouble in the rules. Generally, if you surrender all your properties go to the person who bankrupted you. And that will almost certainly hand them the game. That's why you should only allow surrender once someone has completely mortgaged all their properties so the person who inherits them has to pay the fee to unmortgage it all.
