I was thinking less bandits and more how the player deals with a crisis. Short term loss or gain versus your long term interests. In this case: taking the financial loss, taking a reputation loss, or harming your long term interests. So running out of places to restock if you keep doing it would be exactly the point, while continuously taking reptutation hits would also practically end your game since no one will associate with you.
I know, and I quite like your example. That general idea of the player having to make tough decisions with logical (and somewhat randomized, for the sake of replayability) consequences is exactly where we want to go with the coming event system. This will also afford the player actions of less than exemplary morals – though to what extent exactly is still something we need to figure out. Sorry that I can’t answer more thoroughly to your very comprehensive suggestion, there’s just a lot going on right now.
But restocking now is fairly easy.
Food is plentiful and cheap and you can get enough money from fetch quests.
There is no reputation or fame now so now it will be just choice of slaughtering few peasants to steal their food and few crowns.
Indeed, it would require the introduction of a reputation mechanic first. Like you said, we might want to go with 2 values here. A ‘business reputation’ and a ‘moral reputation’. People might hate/fear you for the atrocities your men commit and not agree with your methods, but you might still be their best shot at getting a job done.