I feel like the biggest problem with monopoly is how long it takes to lose. If you get a bad start, you can find yourself in a losing position just a few laps in. But the game doesn't outright finish you. You need to land on bad squares to slowly get drained. Every lap you take gives you a small amount such that losing takes even longer. You still need to play and pay attention, because the rest of the table might still be in it

Depending on the player group, I've found that losing a game could take 1-2 hours while the initial stage where you realize you are losing could take a mere 15-30 minutes.

It's a miserable game.