Monopoly only drags on for hours if you play by silly house rules like $400 for landing on Go, money for landing on Free Parking, or not requiring an auction when passing on purchasing a property. All of these common house rules artificially extend the game by either injecting cash into the game or slowing the acquisition of property.
A vanilla game of 4 player monopoly should take no more than an hour.
In my experience Monopoly games played by the official rules with experienced players would drag endlessly due to trade negotiations. Typically, whenever a player was clearly in an advantageous position, the remaining players would form a loose alliance, shuffling properties and cash in an attempt to stymie the leader. The leader would fall back into the pack, a new leader would emerge, and the whole process would repeat. Every iteration would require a substantial amount of discussion, proposals and counter-proposals for an equitable but effective distribution of properties and cash amongst the "insurgents". Any thoughts on what we were doing wrong?
Catan at least has the advantage of monotonically increasing building and army points: Given enough time and even barely rational spending, a player is guaranteed to reach 10 points, no matter how alliances form and splinter.
The biggest problem we encountered in both games was the "spoiler": The player who was not in a position to win, but was in a position to determine the winner. Either you try to impose hard-to-adjudicate rules requiring "rational decisions" or you accept that a long-running game may be decided by caprice.
Back when my friends and I played Catan a lot, we developed a simple way to avoid the spoiler effect: running point totals. Games are still played in regular fashion, but your victory points for each session are added up over time. Winning a game gave you an extra VP in the running totals. You can set the constraints to whatever you want: a year's time, 6 months, 10 games, whatever it may be...at the end of the time frame, whoever has the most victory points wins. Put some money down at the beginning, and you've got great sustained competition.
Obviously it only works if you play with the same people regularly, but in my experience that's actually the norm.
The spoiler just adds a level of metagame. You can cripple me early in the game by repeatedly putting the robber on my best hex, but by doing so you've made an enemy for the rest of the game.
*In my experience Monopoly games played by the official rules... Any thoughts on what we were doing wrong?"
I'm guessing you weren't actually following the rules[1]. If you do follow the rules you'll find liquidity gets sucked out of the game by continual reselling because you are only allowed to sell unimproved properties, and have to sell houses & hotels back to the bank at half price.
That rule was followed. Given that we were playing with 3-4 experienced players, monopolies were rare (everyone bought essentially every available property landed on that was still potentially monopolized) and most targeted the sweet spot of three houses. Monopolied properties weren't traded often, but even then that's not a lot of liquidity to sacrifice with ~$800/board cycle going into the game via passing Go.
Once a few monopolies did crop up, it was the remaining unimproved properties that would be swapped most often for ludicrous amounts of money to allow, say, a cash-poor player to build a few houses in the path of the current leader.
"The biggest problem we encountered in both games was the "spoiler": The player who was not in a position to win, but was in a position to determine the winner."
Most, if not all, games of more than two players where players have some free choice eventually boil down to "you can't win it alone. You need help or a blooper from your enemy"
And that is true in sports, too. In any distance running, starting at 800m, athletes collectively make a choice whether to run a fast race or a slow race with a very fast finish. A fast sprinter will not win a fast race, so runners with lower top speed will try to make a fast race. Still, they won't want to be running in the front, they rather have another runner with lower top speed burn energy doing that.
This gets more evident the longer the distance and the larger the advantage of running in the slipstream of an opponent. Road races in cycling are perhaps the ultimate example. If "the peloton" doesn't want you to win, you have to be extremely good _and_ lucky to win.
To me the problem with Monopoly isn't just that it takes forever, but that you can get into a commanding position early and spend most of the game slowly bleeding your opponents to death one by one. Monopoly is a game to resent people over.
To go a little off topic: this is the same style of poison that causes MOBAs to have such toxic communities, exacerbated by almost complete anonymity. At the lower levels, easily 95% of games are decided in the first 10 minutes but last 30-40. Only once you reach professional or near-professional play do you hit the point at which most games end within a minute or two of the winner becoming obvious.
Monopoly's predecessor was The Landlord's Game, designed to teach people about the evils of capitalism. You moved around the board, got robbed, it wasn't fun.
Monopoly changed it up by making it possible to become the evil landlord, and that's what made it successful.
Speaking as someone who was bad at monopoly as a kid, those cash injections helped make the game feel more "fair". The vanilla rules make it really hard for a newbie to win against someone who actually knows how to play strategically.
Now, that doesn't justify turning the game into a 4 hour slog, but it may help to explain why so many people use these "wimp rules".
There are definite "winning" strategies - like acquiring a monopoly on "jail row" and mortgaging all other properties to build it up as soon as possible. But does altering a game so that a child doesn't have to see the optimal moves from someone else do anything positive for anyone playing the game?
I'm going to guess, based on a lot of observation, that most casual Monopoly players of any age don't play strategically. They rely on the dice, negotiate badly (if at all!), buy everything they land on without any master plan in mind, and ignore cash flow until it becomes an issue. These are the opponents most kids will play against in ad hoc games of Monopoly, and in these games, kids will have a grand old time. When the outcome of each dice roll is the most decisive factor in a particular session, a child is at less of a disadvantage.
Also, fwiw, 99% of casual players I've seen overvalue the marquee properties like Boardwalk, etc., and undervalue the oranges, light blues, and reds.
> not requiring an auction when passing on purchasing a property
That rule is so rarely followed I end up in an argument with other players every time I play a game of Monopoly for attempting to play by the rules. People don't even believe that the rule exists, never mind make a conscious decision not to follow it.
The fact games of Monopoly always open with an argument is probably a big factor in me no longer playing Monopoly.
A vanilla game of 4 player monopoly should take no more than an hour.