I can certainly say you are a better programmer than me, if you can automate a significant portion of that process. A lot of the stuff I have there doesn't follow a precise scheme, and it's customized to fit my needs to test this or that, and the things which are more "generic" (like, testing the layered images, changing stats/gold, and so on) are easy enough to add to the travel sphere that I never even considered automating adding new interactions to the room.
Most of the quests which can fail are tied to chapter 1, because I'd like to have some different consequences play out depending on the outcome or if you ignored them. There are a few more quests you can fail, but generally you have tools at your disposal to avoid that situation (some can take you by surprise, but that's what saving is for ;p).
Yeah, I didn't want to spring a new chapter on players, especially since a very limited amount of quests can fail if you don't tackle them before the chapter ends. This way they can take their time and look around, if they want to.
The idea of repeatable quests might be something to look into. Since I have the jobs around the city, I feel like having yet another way to make money would take away from their role, though (which is already a bit marginal).