Alright, time to roll up my sleeves and spout some stuff for your lists!
Biomes:
Tundra, lakelands, coastal regions/strandflats, shrublands, highlands, stony tors, dark pine forests, icefields/icecaps
Settlements:
in hamlets, in floating towns/on house boats, in yurts, in hillforts, in cottages, in vast caves, in stockades
Authorities:
the city council, the merchant company, the town elders, the local baron, The Prophet, the general, the warlord, the local magistrate
Antagonists:
a rival township, a local hedgewitch, troublesome settlers, a mining company, a rogue military unit, a criminal gang/organised crime network
Issues:
land rights, grazing rights, legal jurisdiction, the building of a bridge, right of safe passage, tolls, taxation, religious freedom
Complications:
pirates, a nest of vipers, a pack of hungry wolves, rogue wizards, a warlock, a haunted ruin
Jobs:
loot and pillage, defend the locals, occupy the area, root out troublemakers, pacify the locals, depose a local ruler, hunt down a criminal
Tilts:
supply lines were cut, intel was bad, we lost our scouts, a terrible storm struck, natural disaster,
Big Tilts:
our employer betrayed us, our real enemy was someone different, the authorites and antagonists were conspiring together
.... I hope those are useful to you!
Re: general feedback. You've obviously got some time-skips in the narrative you're setting up with this bot - telling the entire story with all the twists and turns through a bot would be tricky in any case - but to my eye the transition from job question->setup question->tilt question looks a little bit abrupt? Perhaps it's worth having some sort of positive reply from the bot after the player has specified what the job is, and maybe something to fill the gap between the setup ("everything is in place and looking good!") and the tilt ("oh no we've been through something terrible")?
It doesn't need to be a big thing: just something to bridge the gap between everything being fine and everything having gone terribly.