If Monopoly is like your FAVORITESEST GAME EVAR, I apologize. To each his own, and all that. But I'm still going to tear it apart.
That's a lot of freaking Monopolys
The Lack of Meaningful Decisions. Much like in fiction, games are made interesting by meaningful decisions--choices the protagonist (in this case, you) makes that affect the outcome of the game. In Risk, for example, you must decide where and how to allocate your forces, while in Candy Land you just do what the card says.
Monopoly is closer to Candy Land, unfortunately. There are decisions to be made, but they are few. Do you buy the property you landed on or not? Do you buy houses/hotels? And of course, how do you get your brother to give you Boardwalk in exchange for Baltic and Waterworks? With the exception of property trading, these decisions are usually non-decisions.
Unbalanced Gameplay. Rents begin at $2-50 (in our version), which, with your starting cash of $2,000, is negligible. Rents only get interesting around 2 or 3 houses (which is why "Do I buy houses?" is a non-decision: if you have spare money, then yes). The problem is the rents of 4 houses or a hotel is HUGE on most properties, and it costs no more to get there than to get to 2 houses. All it takes is for some sap to land on your hoteled Indiana Ave once to cripple them. Which leads to the third problem...
The Long, Slow Crawl to the End. So he lands on your hotel and loses all his cash and most of his houses. That's okay, he can still come back if you land on his properties, right? Well, no. He had to sell his houses, so the rent he gets from you now is (as I said) negligible. Certainly not enough to afford your four-figure rent and--whoops!--he landed on it again.
Game over? Well, no. He still has houses to sell, properties to mortgage, math to do. He has to wait until ALL his resources are gone. Why? Because them's the rules.
Of course house rules can mitigate some of this, but Parker Brothers is so convinced of the goodness of their game (or maybe just the money they can make from it), that they haven't changed the rules in decades (or God-knows-how-many Intellectual Property-opoly versions they've made). In fact, they've made it worse recently by adding a computer that knows nothing about your "rules."
So what do you think? Is Monopoly a good game and I'm just missing the point? Enlighten me.