The specific purpose of the OG version of Monopoly was to infuriate the players and make them resent the microcosmic system of economics the game presented. It was literally just a propaganda piece that set out to enrage it's players. Everyone still considers it a game.
While I agree with the general comment, this part made me laugh a little. I find that games are incredibly easy nowadays, there is little "effort" to actually reward.
To me it's a worse trend than the lack of "pessimistic games". Building a culture of "what do you mean I didn't succeed after the second try? But I'm entitled to make it to the next level!!!!!"
I might be very cynical, but I think it hurts society a lot. Kind of similar to all these TV shows where the main character transitioning from being a waiter to sales executive or director of marketing in 2 or 3 seasons.
While I agree with the general comment, this part made me laugh a little. Games (and TV/movies) are designed to cheat your brains reward system and make you feel like you are achieving something. This is why they're fun to play/watch.
I would argue that it's more insidious to require more work out of the player because it's prolonging the inevitable realization that you're not actually accomplishing anything. Games that cut right to the chase and reward you from minor accomplishments allow you to get that quick rush you were looking for then get back to your life.
Think about people playing World of Warcraft (especially vanilla days), sinking untold days of play time into grinding out gear/rep/gold. What are they actually getting from this? Versus just about anything else they could be doing with that time? The easier games make it to be rewarded, the more honest they are as a game. You could argue that you want a game to feel like a job because you can't get that satisfying sense of hard work paying off in real life, but I seriously doubt anyone would be happier with a productive, rewarding game life than a productive, rewarding life-life.