Speaking as a player (most of the time) I love making things worse for my poor character. And I send my evilest ideas to my DM. Who then makes them heartachingly worse. It’s great.

Diabolical. I’m thrilled by the idea of it happening to someone else.

I built a one-shot around this idea on a heavily-modded Tiny D6 system, letting people choose which of the 4 they wanted to be with variants like wealthy or scientific Victorian, captain or gunner pirate, disgraced or retired Samurai, cattle driver or 49’er, and so forth. I set it in San Francisco to get some good conflux of cultures.

Of my 4 players, 3 of them chose to be rich Victorians. facepalm

Our player who likes doing this to the DM: “So they’re giving us horses? What are the horses’ names?” Our DM: “…no. You choose.”