Simply put, I don't think we can actually sympathize with his situation because we probably don't understand it, or at least he won't think we do. This guy has to try and stretch money as tight as it can go to try and make sure everyone has food, shelter, so on and so forth. He probably gets complaints day in and day out from people who don't have enough, who need more, stupid spats due to stress because of the current situation, making sure he doesn't fuck up and ruin everything going on, making sure other people don't take advantage of the situation to fuck them up, etc.
Simply stated, while we do indeed have the weight of community on our shoulders and the threat of a horrible death if we fuck up, possibly the death of the settlement if we mess up, this guy feels it more than us because he's actually down there in the trenches dealing with it day in and day out. How often do you think he's able to go for a drink, or watch a movie, or tell jokes, or make horrible plans for a cheesy anime in an ill-fated get rich quick scheme?
Dude deals with stressed out people every day trying to make sure that not only do they have enough to pay off the land they're on, but also that it gets fixed up, they have food, water, and possibly some comfort. He has to deal with people who would still be grieving, still angry at the hand fate dealt them, still in shock from the whole situation.
My take on the situation, at least.