I think the difficulty with chapter 2 is probably the old problem I was notorious for when running some of my more complex pen & paper RPG sessions. Namely, I would have a decent plot, various ideas, but the general scenario meant that instead of exposition to the players I wanted them to discover the links and figure it out themselves. As it turns out, this is way harder to do from the other side as a player and what I thought were starkly obviously clues often were skimmed over without a second thought. (Incidentally, I solved this in-game by having an NPC be a subtle guide which corrected for my oversights.)
You come into chapter 2 somewhat aware that you need to solve this docks crisis in some fashion. Whether you want to solve it in favor of the guild is dubious and up to the player, but either way you soon realise you have to break the stalemate in some fashion. At this point you can talk to various people and do some things, but it feels like that myself, that is the player, is not actually the protagonist here. Why? Because I am not sure what outcomes my choices will have. Sometimes this is fine - some choices are morally grey, but these weren’t particularly moral choices and I felt there were a few too many here for me to actually feel in-control of what is supposedly a trained stealth creature. What you can do with the beneficient candidate is fine - this rapidly becomes an opportunity as you talk with them. It has a natural flow, they are an artisan, they care about their craft but they need money and are getting desperate trading with the East etc., so what comes next feels reasonable. The humanist candidate has a surprising outcome (or at least it was surprising to me) if you happen to mention Gi to them, which significantly affects the outcome. This consequence can’t be judged and just seems to happen. On the other hand, talking to the auteur results in a sudden opportunity to actually use your stealth and infiltration skills (whereas if you just enter the guild hall from the alternate entrance you do not get these options). I inherently went for the alternate entrance as not only did that sound useful, but met with my mandate as a stealth agent within this scenario. However, it was perplexingly un-useful. I used my meta-knowledge of the fact this was a game to deduce the reason it gave me no options to poke around the offices was because I had to do something else first. This is a little immersion breaking and again another reason why I say I didn’t always feel like the actual protagonist in this chapter. Personally I think what is needed here is to either fully open up alternate avenues or steer the player in the right direction by removing them if they do not make sense, make the consequences of choices a little more obvious, or perhaps make the advice given by Trullo (or some other) a little more useful and aware of the player’s scenario. Chapter 2 is amazingly ambitious for your first major chapter, I might add!
Okay, that has clarified the problems about that box in chapter 2. I think the confusion is probably arising from people not being able to understand whether their ability is too low or the resource is too low. There is no real indicator either way, or at least none that I deduced. I’m not entirely sure how this could be evoked in game - if you’re just not good enough at mechanics, perhaps you could just inform the player this is clearly out of their league, but if there is not enough resource, I don’t know, do they tire? Not enough concentration? Not enough tools?
I am very much looking forward to another full run-through. Unfortunately I failed to get anything that classed as a vaguely happy ending the first time, not that I feel bad about taking that play-through. Sometimes it’s those kind of experiences that stick in your mind more. I still feel quite strongly about the characters now, which should be interpreted as a good thing. Reading back through my last post, I am unsure if I expressed quite how much I liked it, but I assure you I would not have gone through the effort of nit-picking on these small things and providing feedback had I not felt it worthwhile.
All the best!