Another Himedere checking in. I love setting up situations where the players and/or the characters squirm in anguish about what to do.
My favorite so far was an estranged princess living as a man and hostel owner. He had turned his back on the throne and wanted little to do with it. As a bonus he was the only child of the king’s only remaining child. Fast forward a bit and he needed a (legal) favor from the king. Went to court and met with his grandfather. The king would do it, no strings attached if a) he returned to court and resumed his duties as prince and b) sired an heir.
There were a good thirty minutes of the players anguishing if he should accept while going deep into character motivations and the setting. During that game I don’t think I did as much concrete worldbuildning as during those thirty minutes. I loved it, the players loved it. Great time.
Shawn Tomkin’s Ironsworn series. Delve I regularly use for setting up point crawls. Ironsworn/Starforged/Sundered Isles have great collections of random tables, I use the book thematically most fitting for the situation at hand. The core tables of Action, Theme, Descriptor and Focus all get heavy use.
Kevin Crawford’s [SOMETHING] Without Number series have awesome tables as well. These however get more use when I need more detail. Prep stuff. Again most thematic book is picked first but I do have used Cites (cyberpunk) for fantasy cities.
When I want to create background for “medieval fantasy” characters I pick up Burning Wheel and burn something up. Through that I get a good selection of relevant skills to sue (for flavor)
Anything related to cosmos and mythology I say HELLO! to my growing collection of Glorantha material. From cult books to magic tomes and Atlases.