Having random schedules is a double edged sword. As you said, it feels natural when NPCs are not totaly predictable, but having too many variations will make them harder to remember. Set schedules are less natural, but I can add more of them to get the best of both worlds. I'm experimenting with the idea of separating all schedules (For example, Billy will visit the inn every eight weeks instead of every four weeks. Suong will spend more time in the forest and sometimes be without George.) so they can feel a little more natural but still be in a set pattern an thus easier to predict and remember instead of relying too heavily on status and world map screens.
As for your dungeon feedback, I don't think I get what you are saying. You open a chest and you get a small popup that tells you that you got a +1 points. And about a second later, the "point shop" shows up.
