Jeff’s life is tragic overall, but he once accidentally fell asleep at the guards tower and accidentally kicked over a lantern which signaled an enemy attack. The entire town spent a day preparing for a war that wasn’t there.
As for contracts, the general rule of thumb is that missions/contracts that cost money, give favor, and vice versa. So it’s a balancing act of getting what you need and when you need it and figuring out what is a good deal.
Thanks for playing!