I never played enough Settlers to pick up on this but I totally get it with Monopoly, and I feel like this is bad game design when it happens.

Monopoly feels like the game might take 4 hours but you know 20 minutes in that you're hopelessly behind and cannot come back. Then it's just 3 hours and 40 minutes of torture.

If you're doomed to lose the game should be over quick.

In the case of Monopoly that feeling is the point of the game:

> The history of Monopoly can be traced back to 1903,[1][8] when American anti-monopolist Lizzie Magie created a game called The Landlord's Game that she hoped would explain the single-tax theory of Henry George as laid out in his book Progress and Poverty. It was intended as an educational tool to illustrate the negative aspects of concentrating land in private monopolies. She took out a patent in 1904. Her game was self-published beginning in 1906.[9][10]

https://en.wikipedia.org/wiki/Monopoly_(game)

> If you're doomed to lose the game should be over quick.

I think most people are in this situation in life, but would disagree with you. The game itself was intended as an educational tool to illustrate the negative aspects of concentrating land in private monopolies, hard to get the message when it's over quickly.

> Monopoly feels like the game might take 4 hours

For what it's worth, if you play Monopoly by the actual rules, and you don't act stupidly stingy on your trade offers, a 4-player game of Monopoly shouldn't take more than 30-45 minutes.

The problem is, people of course don't like losing, and everybody loves a comeback story. So people play with house rules that constantly inject extra money into the game, which prolongs the game's purpose: For all the wealth to consolidate to a single player.

House rules in Monopoly are so common that a lot of people don't even realize they're playing house rules!

Do you give money for landing on Free Parking? You're playing a house rule.

Do you give $400 instead of $200 for LANDING on Go? You're playing a house rule.

Do you allow purchasing Hotels when there aren't enough houses? Do you allow building to not be even? Do you use some sort of object to act like a hotel because the game only comes with 12 hotels in the box? You're playing house rules. The fact there are only 12 hotels and 32 houses was a deliberate design choice to force players to trade and allow one player to horde all the houses and hotels.

You can't mortgage properties that have buildings on them. You must sell the buildings first, and you only get half of what you paid for them from the bank. When you unmortage, you have to pay an extra 10% fee. You don't collect rent on mortgaged properties. If you play any differently, you're playing a house rule.

Rolling doubles 3 times sends you to jail. That's actually NOT a house rule!

Speaking of jail, you DO still collect rent while in it! This means that deliberately staying in jail can actually be a strategic move if another player is possibly about to land on your dark Green properties (Baltic, North Carolina, Pennsylvania) while your opponent owns the Oranges, which you're likely to land on immediately after leaving jail.

Don't get me wrong, Monopoly is a shitty game for many reasons, but "Games take 2+ hours" is not one of them unless you're playing it wrong.