Historically is a very broad term. Ptiched battles and bloody city assaults happened more frequently in antiquity than during the middle ages. In the times of knights and chivarly, long, drawn out sieges were the norm. They would most likely end with some form of parlay and a relinquishing of this and that between the nobility involved in the fight.
Pitched battles and siege assaults were bloody and costly business, and your dirt farmer levies were going to break morale and run at the first hint of trouble. These were not disciplined Roman troops or blood thirsty proud warrior societies like the celts, gauls and the germanic tribes. That's why in the middle ages the most prominent battles we remember were actually the most rare type of battle - like the siege of Acre, the fall of Jersualem etc.
That being said, settlements do, in fact, turn into deathtraps for the AI in R2TW. Since unlike in games like Rome 1 and Medieval 2, here the conquering army loses all it's movement points upon entering the settlement. In the previous games you gould go in, sack and run away. Here you go in and you're stuck, and the next turn the player comes with two stacks and splatters you. I know that's how I play. Especially now in my Avernii campaign, I'm making great use of the Celtic Ballista units, raining fire on the clumped up low morale barb units just sitting there inside a settlement or fort.
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