I’ve had to do a lot of traveling between cities to progress. I’ve tried to do as many 1 skull contracts as possible, after about 7-8 I started seeing contracts from the factions. Now I frequently get 2-3 skull contracts popping up in the cities. Try to look for footprints on the ground and follow them, most likely you will run into bandits that you can farm for loot. The maps are random so I cant tell you where to farm, but try to stay in an area that you know well so you can kite back to the city if its a hord of orcs or something that could wipe your team. Always save game before a battle :).