Okay, so, there’s thief in your group and they want to infiltrate the tent of an officer from an opposing army. Its in the middle of the camp and you want to make it hard, but from your point of view, it would be a good thing if the thief was able to do it.
So, lets suppose the player rolls 2d6 and has to get at least 7 to succeed. They get +2 from their.. skill. Whatever. First, you want them to roll for moving into the camp. Then you want them to roll for moving through the camp. Then you want them to figure out where the tent is and roll for that as well. Then you want them to roll for entering the tent. They’re pretty good at what they do, so this should work, right?