Happy to help :)
It seems the problem is not only with the quest difficulty skulls amount but with the difficulty of the enemy itself. After starting an other new game but this time not going thru the full tutorial the regions only quest was the same werewolves, a 2skull one this time. But since did not follow thru with the tutorial have less men and equipment than the other time. Result still the same.
Potential issue can be with the caravan quest. When it is taken it does not account for the roaming armies that it can encounter. While in a caravan mission we ran into a raider group. At day 3 it is not realy what you wish for. The group came to the road and massacred a caravan before ours then attacked us. We did win with half of men remaining, still we could have run into stronger enemy potentially, that would give no chance. The caravan hands were in even worse equip than my guys wearing 20-30 armor knifes and clubs. So on day 3 my four remaining men changed their 40-50 armors to 100+ ones.