A lot of good points but I still think Monopoly is a pretty poor game by design.
Games are about decision making, and there is very little decision making to be had in Monopoly (Real or not). There is no strategy shift for the opening, midgame, or endgame. There's no secret scoring or clever traps, there's no imperfect information of any kind. Assuming dice rolls are the same, playing against yourself and playing against another person or playing against a computer will have pretty much identical outcomes.
In other words, if you want to play Real Monopoly with me, just go ahead and play against yourself and do the rational thing for me if a decision comes up. Let me know if I win.
Even in the shorter form of the game, the winner is usually apparent quickly and then there's a long march that resembles the Trail of Tears more than it does board game turns.
If you're going for an interesting board game, instead of Real Monopoly, I'd highly recommend:
That's probably because the game was never designed to be fun. It was designed to be a lesson that demonstrated the negative aspects of land monopolies, and that a land value tax was a good idea.
Whereas today, it teaches the much more fundamental lessons that the rich get richer and the poor get poorer, and that top hats can go faster than cars.
There are lots of good games out there. I'd tend to recommend Agricola and Power Grid also in the economic theme, but you'll do fine just browsing the recommendations at Board Game Geek and seeing what strikes your fancy.
http://boardgamegeek.com/
I own both of those games, and after play Agricola, I've decided that it's just too aggravating (too many tough tradeoff decisions) but Power Grid is a favorite, and in a lot of ways, if you are interested in playing Monopoly, you'll find Power Grid to be 100x more fun.
It's funny that you mention Settlers, since every time I've played it's always been quite obvious after the initial pieces are laid who will win hours later. If you don't have the good spots, it's a painful, slow grind to defeat.
However, it is a hugely popular game, and I'd love to know why.
I suspect that you're playing it wrong, or with the wrong people -- particularly if it's taking you hours to play.
Typically, there'll only be one or two really good spots (say, 8-10-5 or something). The players on those spots will/should get a disproportionate share of the baron, both because they have more cards and because they're in the lead and need to be dragged down to everyone else's level.
The game then becomes an issue of trying to get good without appearing so and picking the right time to make your move, rather than 'I have x points/regions, therefore I win'.
Sounds pretty similar to the Monopoly rules, now that I think about it...
I think it's popular because it is mostly random chance with a veneer of strategy. It's a clever game in that it equalizes people who think about it a little with people who think about it alot, but gives both those groups an edge of people who don't think about it at all. This makes it more accessible to people who wouldn't otherwise consider themselves serious gamers because if you try, eventually you'll get lucky and win.
If your game of Monopoly includes very little decision making, you are playing it very wrong and it's no wonder you don't like it. I have gotten the absolute worst rolls, ended up with two properties and still managed to negotiate my way to a win. That means that other people were making poor decisions.
The imperfect information in Monopoly is what you're thinking in your head. I've traded things with two or three other trades in mind that the other person couldn't have known I was going after. Or, traded someone a Monopoly they thought was a good deal, then sold my hotels to use up the remaining houses so they can't develop it.
And, there is ABSOLUTELY a strategy shift for the opening and endgame. Don't believe me? Try to develop the Green monopoly first.
The best version of Monopoly I've played is the Mega version. A third dice speeds up the game start and finish by forcing players to move to the next unowned property, or to the next property where they must pay rent.
http://en.wikipedia.org/wiki/Monopoly:_The_Mega_Edition
+1 for those who recommended Settlers. Ticket to Ride is also fun, and Diplomacy does not have to destroy friendships. (Anyone willing to devote 5-7 hours to a game is a friend forever, no matter how long I remember that time they switched sides without warning and wiped me out.)
There's plenty of imperfect information - I don't think you're required to reveal how much money is in your hand at any point, much less how much you'll pay for a particular property, and thus plenty of opportunity for richer players to screw poorer ones out of the property that they've landed on.
There is a surprisingly good implementation of Settlers of Catan for iPhone, I'm playing through Seafarers expansion scenarios and enjoy it a lot.
Fun fact: Xbox 360 version has "equalized dice" setting (don't remember the actual name) which makes dice less random so it would have better histogram. This setting removes some frustration from the game, like you settling on two sixes but getting only eights benefiting the enemy, but obviously makes "lucky wins" less likely for you as well.
The iPhone version has this too: set Dice Mode to "Stack" to get a perfect distribution (as though you were drawing from a stack of numbered cards rather than rolling dice) and "Stack5" for a slightly less perfect one (as though 5 random cards were removed).
> This setting removes some frustration from the game, like you settling on two sixes but getting only eights benefiting the enemy, but obviously makes "lucky wins" less likely for you as well.
I've played regular board-game Catan about 10 times, and every single time either 6 or 8 has come up way less than it "should". It's been roughly equal whether it's helped or hurt me, but it really takes some of the enjoyment out of the game when people fight for those spots, only to have them be worthless.
+1 to the recommendations of Puerto Rico, Settlers, and Power Grid. Everyone I've played those games with immediately forget about Monopoly/Risk/etc and ask when we can get together to play again.
I often play Neuroshima Hex on my iPhone, it's great.
An interesting game that is very similar to Monopoly in a lot of ways is Rail Barron. However, in Rail Barron there are more choices to make (whether you pay someone else is not merely dependent on a die roll), which makes the game more interesting, and the end game generally goes much faster, making the game less of a chore.
Games are about decision making, and there is very little decision making to be had in Monopoly (Real or not). There is no strategy shift for the opening, midgame, or endgame. There's no secret scoring or clever traps, there's no imperfect information of any kind. Assuming dice rolls are the same, playing against yourself and playing against another person or playing against a computer will have pretty much identical outcomes.
In other words, if you want to play Real Monopoly with me, just go ahead and play against yourself and do the rational thing for me if a decision comes up. Let me know if I win.
Even in the shorter form of the game, the winner is usually apparent quickly and then there's a long march that resembles the Trail of Tears more than it does board game turns.
If you're going for an interesting board game, instead of Real Monopoly, I'd highly recommend:
http://en.wikipedia.org/wiki/Puerto_Rico_(board_game)
http://en.wikipedia.org/wiki/Settlers_of_Catan