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.”
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.
Rolled a character for a one-shot (using a bot on Discord) that got 18, 16, 16, 16, 15, 13 once. It felt like cheating.
That being said I really enjoy playing a character with one really bad stat. Like 5 or 6.
My current rogue started out sharing loot fairly but it’s become a running joke that she stashes so much she jingles when she walks. To be fair, half of the party actively don’t want money and she’ll share when asked (if she can’t get the five-finger discount on whatever the party’s trying to acquire) so essentially she’s acting as the party bank.
Diabolical. I’m thrilled by the idea of it happening to someone else.