2) First job exploit
Even the very first job can be exploited when a caravan starts from the starting town. It is a free win scenario.
Sky calls it “exploit”, I call it “strategic genius” on Sky’s part! :)
I think what he meant by that screenshot is that when you first start the game, and there is a caravan close enough to the nearby bandit lair, you get the help of the caravan to take out the lair. In my opinion, this is relatively rare — never had the opportunity myself — potentially exploitable, but I think not really a big deal (maybe a quick fix would be to make sure the starting town lair doesn’t spawn close to a road).