Hoo boy, you're opening up a huge can of worms here. While Monopoly is considered a timeless classic by most people in the US, it is also one of the most roundly criticized board game designs of all time. In the past 100 years, the art of designing board games has come along way, thanks in part to a German board games renaissance, the most popular product of which has been The Settlers of Catan.

Most modern board game enthusiasts see a lot of flaws in Settlers as well, but they recognize that Settlers and its like correct four major problems with Monopoly's design:
* players are eliminated from the game: in Monopoly, once you're bankrupt, you just have to sit around waiting for the rest of the players to finish
* the conditions for winning the game in insufficient: only after all other players are bankrupt, the remaining player wins, causing games to go for hours and hours with little end in sight if two players are nearly tied for the lead
* luck plays too much of role: you roll two dice, hope you land on a property that's not owned, and hope you have enough money to buy it
* lack of interesting decisions: during the game, if you are lucky enough to land on a property that's up for sale, there's very little reason why you wouldn't want to buy it (other than you can't afford it)

The best games attempt to avoid player elimination, define the end of game such that the game lasts a reasonable amount of time, reduce the amount of luck involved (but not necessarily eliminate it all together) and provide the player with as many meaningful choices as possible (often, in a well designed game, you'll have to make many decisions during your turn, each of which might be completely agonizing.

For a good example of an improvement in the hotel buying genre of games, see Sid Sackson's Acquire, from the 1960s. It's old enough to be considered a classic too at this point, but has a much better design.

So! If I were to change Monopoly's ruleset, I'd start with trying to eliminate some of the luck factor. Maybe instead of simply rolling dice, in order to move a space, you first roll a dice and then may pay to move up to that many spaces as you rolled, provided you pay a set amount of money for each space you move, reflecting the high price of gas today. For example, you roll a 5: now you must move 1 to 5 spaces, and moving 3 spaces would cost you, say, $30.

I would have a better end game rule: once the last hotel in the box has been built, all player take one more turn then the game ends. The player with the most money at the end of the game is the winner. This reflects the volatile housing market.

Instead of being eliminated, players can take out of loan from the bank, which they would need to pay back. If the end up with a negative amount of money at the end of the game, they're definitely not going to win. This would be a reflection of the credit crisis.

Because of the new end game rule, that the player with the most money wins the game, players now have more decisions to make during play: will investing in housing really pay or, or will it just affect your bottom line, giving you less cash on hand. If you notice that the pool of hotels is beginning to run dry, you'll be less likely to spend your money on future investments.

All these modifications are simply off the top of my head. For them to be implemented well, I'd need some time to think through the changes, test them out, and make sure they don't break the game completely.

But the one rule for sure I'd change is: no free parking!

Mr. Moneybags, the names of the properties, and the cute little dog.

Clyde