I like running modern-day settings. I want to run 2021 near the "end" of the pandemic. I try to run simulate the Philippines: with its corruptions, the vilification of the poor, cycle of poverty and abuse, sex trafficking if the Players go there, the good nature and hospitality of the people, the trolls and the paid thugs, the police violence, the opportunities and markets that need the skills and cunning, the Oligarchs, Syndicates, and Organizations that mix biz, pleasure, and then ambition, misinformation, culture, and ideals.
The goal is let people go around and explore areas they are afraid of, to risk-averse for, and to find courage and the forces that push society and conditions towards their consequences.
I consider it "fun". Fun that I don't have to pay the consequences of really doing the right and hard thing. Seeing all the ways I or the players can fail as they can see things think things through, Or see them get caught up in the emotions and passions of a cause that hopes to fix or change things.
These games help me I see an Action and see all the Technical DEBT of an action. I get more familiar with how I'm surprised. I learned to anticipate the Twist, those moments we choose to be decisive and allow ourselves to focus on one thing - to brace for the threats we chose not to tackle with our scarce attention.
I like it with the Flaws, which get less hopeless as I get the mental practice of tackling them. The work needed to make things change and improve makes me less anxious or fearful of the future. Even the disappointments and the failures become nuance as I happen to learn one new way things don't work.