Pillages, Raids and Extortion
Medieval warfare was quite primitive, at least insofar that there were not a lot of battles and the troops spent most of their time stealing from civilians, or looking for an opportunity to do so. This was the Golden Age of Pillage. Armies lived off the land, or, rather, the local farmers and whatever food and valuables these poor folks possessed. Soldiers had to eat, and they wanted to get rich. Pillage, raiding and extortion are how these Medieval activities are represented in the game. In the game, pillaging means an army commander has ordered his troops to spend a week or so searching through a fief for valuables. This would also include food and livestock, but everyone was really eager to find gold and jewels. The locals would flee, if they could, either hiding in the woods or making for the castles and walled towns in the area. Some locals would be killed, and great damage would be done to the area as the soldiers often burned down what could not be carried away. Naturally, the local troops would attempt to resist the pillagers, and if the fief were populous enough, and the pillagers few enough, the invaders would be chased out before any damage could be done. A raid was a shorter version of the pillage, wherein the raiders would ride quickly through an area, taking what they came across and quickly moving on. It was more difficult to defend against a raid, because the enemy would be about their business and gone before the local troops could do anything about it. Extortion was, so to speak, a more civilized form of pillage. The enemy army sent someone ahead to tell the locals that they would be spared a pillage if they paid off the enemy. Sometime this worked, sometime it didn't. It all depended on how many enemy troops there were and how many soldiers there were in the area being extorted.
The difference between pillaging and raiding is that one is larger than the other. That is, pillages take longer than raids, net more than raids, drop more loyalty than raids. That is when it is compared to 1 on 1.
You can only pillage once a season in the fief, you can raid 3 times. Best is to pillage and raid all you can there and then move on. This will decrease your stature a small bit and give you some cash to work with. Each pillage takes 7-15 days, each raid 2-5 days. You have no control over exactly how long this will take, as your troops will be scattered all over the place and will wander back at a speed dependent on how much loot there was to be found. The amount of loot you, personally, get out of a pillage or raid depends on your stature. If your stature is 9, you get 45 percent, if it's 1, you get 5 percent.
The best type of force to use in this type of combat is 200 - 500 men. you won't take heavy losses, nor will you create heavy losses for them. but we aren't counting bodies here, we are counting loyalty points. Think of how hard it was for you to raise your loyalty and with someone beating up on the lands it is even tougher. Keep in mind that the amount of money you get from pillage or raiding is dependent on your stature.
The keep level of the fief is not always the best factor to consider. Check to see if there is a high negative expense value. If there is, it means that there is a good manager there. A typical pillage reduces the fief loyalty by about 20%. The amount of loot depends on your stature (which will decline a bit each time you pillage, the church, and society in general, frowned on pillaging.) You will get more money if the garrison comes out to fight. One long term benefit of pillaging is that the Loyalty of the fief will decline. Thus one player can move ahead of the main army, softening up enemy fiefs with pillages and raids (a quick form of pillage that takes less time, and garners less loot) so that the pillaged fiefs are easier to take.
If you lose a fight with the local garrison, you are retreated up to six hexes away, generally in a straight line. Pillaging, successful or not, takes at least several days.
Extortion gets you money from a fief, does not cost you any stature and does no permanent harm to the fief (other than removing money that would otherwise go to the owner.)
There is also a chance that you'll get lucky. Each pillage or raid has a 30 percent chance of your lads coming across something really valuable. When that happens, the take is 2-10 times (it varies randomly) larger than normal.
There is also auto-pillage , when you remain in a fief over an update.
Pillage and Raiding Probability Tables and Software Procedures