This being said, randomly generated raid dungeons would be interesting. An example would be learning a local group of bandits has created a fortified camp somewhere from which they're raiding, and if the player were to destroy the camp then bandits would temporarily quit spawning in that area. For all intents and purposes though, I would treat it as a special encounter party with speed 0, and a unique list of battlemaps. (Mountain caves, forest hideouts, etc. could all be used.) At any rate, it would be interesting to raid a Robin-hood styled hideout, with archers sniping you from treehouses and whatnot.
Another Raid-style scenario could be establishing a Prison Break. In a castle or town with sufficient number of prisoners, one could after sneaking in (or being thrown in the dungeon) attempt to break into the prison. Depending on how many soldiers were not killed OR Koed in the process (at least until they get over the walls), that many would be available for recruiting. After the break though, the player would not be able to re-enter the town for awhile, and the relationship with the town would drop. Also, your relation with the faction would drop about 10 points, that if you were neutral, you'd probably be at war with them.
Finally, update the siege format a bit. After breaching the walls, make the rest of the fight obviously a street fight and not just a fight similar to bandit traps or being caught sneaking. Add burning wagons/barricades as appropriate, maybe have townspeople running away from both combatants. Also, rather than making it "beat everything in town...beat everything in castle." make it that the castle is the primary area the defenders are centered around, and expand the castle that if you can fight your way to the top of the castle and plant your flag, you win. Ala Lords of the Realm 2 or so.
