Just to close that discussion:
I don't think it glitched out on me. It just so happened that I accidentally skipped the encounter on the road where James (is that the thief's name?) gets beaten up, because I just jumped down the rocks and came to the town without ever advancing the quest. I don't even remember why I did this. I think I was just curious whether I could go down the mountain that way or would die to fall damage or something
. It as really weird. The guards at the gate turned Kalyskah away and she was not given any options to reply. At the time I thought that is just how it is, because you can of course enter the town from the side and simply bypass the gate encounter, so I didn't really think anything of it.
I don't remember if there was a quest marker on the road for that first crucial encounter though. In general it might be helpful to implement something like that (maybe it was in and my peanut brain just didn't see it).
As a result, I also had the Demon Girl along with me in town. That was really annoying because she kept stopping in door ways, blocking the way
So I assume that a trigger in the quest line was just missing or something. On a second playthrough, I followed the road, got the encounter and everything worked as intended.
On a different note:
Are there plans of having a map in game? Would be really helpful to navigate the world, especially if it gets bigger at some point. Or maybe there already is one and I just didn't find it?