Monopoly: Wheeling and Dealing
The player best at wheeling and dealing is likely to emerge the winner in Monopoly. Dealing is more an art than a skill. It takes a certain understanding of the nuances of the personalities of the other players sitting around the board, as well as how your own personality comes across. In my own games I have found that the best course, especially when playing with the same people frequently, is to gain a reputation as an honest player. Offer fair deals that can be advantageous to both players (just make sure it is a bit more advantageous to yourself - if possible).
The realities of the buying phase of the game are going to dictate the terms upon which you are going to be able to trade. Realize that failure to gain a color group monopoly will almost surely be your doom. However, you should not allow this fact to make you desperate, as the other players will all be under the same apprehension. Simply strive to gain the best color group possible considering what you have to begin with and the players most amenable to bargaining. Keep in mind, even though Connecticut Avenue will give you a bigger return on investment or that the orange properties are perhaps the most frequently landed on, Boardwalk and Park Place are still the most valuable properties on the board. One or two times landing on either will break almost any player and enhance a player's ability to bargain for more property. The value of a monopoly is pretty much proportional to its distance from GO (moving forward).
Having all four Railroads is nice, but most color groups, once they have been improved, are worth more (an exception is Mediterranean and Baltic). The Utilities are never a factor late in the game and should only be considered a bargaining chip to gain better properties. Watch what other players have money-wise and, when bargaining, try to leave them as dry as possible to prevent them from improving too much when they finally do gain a monopoly. Sometimes you will have to swing three-way deals to get what you want.
If you feel pressured to make a deal, because you are among the last to acquire a color group, you will be tempted to make offers that may seem desperate. Try to keep the deals as even as possible. You don't want your opponent jacking up his prices just because he knows you want something he has. Much will depend on your demeanor. Bargaining for property in Monopoly is a lot like real life. If you show your enthusiasm for a property owned by another player and tell everyone how you plan to improve it, you are likely to pay through the nose for it. Stay cool, and feign as much indifference as possible.
If you offer a deal and the player to whom you make a proposal is skeptical, simply offer the inverse bargain to show he really is getting a good deal. For example, if you offer to trade two of the orange monopoly for Park Place, and the player acts like a stone wall. Try turning it around and say, "Well, then, I will give you Boardwalk for St.James Place". This seems like an outlandish bargain to your opponent's benefit, but the relative position of the players might make it a tremendous deal for you, especially if you are in a position to improve your properties and your opponent is not.
It is a misconception that players may only initiate a bargain on their own turn. The fact is, bargaining can occur at ANY time. Some of the best time to gain property is when other players become distressed. When they land on a space with a large rent (your property or someone else's) and start shuffling dismally through their money, offer cash to make up the difference between what they have and what they must pay. Sometimes you can pick up properties for a song. You can even buy properties in mortgage. If you do so, though, you must pay off the mortgage, or a 10% interest fee to the bank to keep the property in mortgage. Make the distressed player see that this is to his or her advantage. You should not always worry about which property you are acquiring. Remember, all property can produce income, and a piece that is not valuable to you is nearly always valuable to someone else and will likely prove to your advantage to hold (to prevent another player's monopoly) or to trade (to enhance your own position).
Try to be the first to gain a monopoly. And if you gain an early "natural" monopoly (where no trading was needed). Try to stifle other trading as long as possible, while you reap income from your advantageous position.