*Sorry duplicate post, sent the first before i meant to and this is my first post so it has to get approved*
Great thread! I'd like to contribute. I think I found a new way to kill the entire caravan, get all their loot, and live to tell the tale!
With this trick you get 348 gold, plus an inventory worth of gear, and keep the Disappointer. Though it is a little buggy, lol.
http://i.imgur.com/ujc6psw.jpg
So I think the "standard" way so far has been to send calisca to kill the merchant. However, I found it better to send her after the caravan leader, while you stand at the lower left of the camp near the merchant but in the safe place in the trees. Calisca will die without killing the leader and the guards, but most of the weak caravan people will come after you. You can easily take them out with some AoE, while the caravan leader and guards will stay put at the top part of the camp.
So here's where it gets a little buggy. Even though you don't have the leader's aggro, the fight wont end. You can run anywhere on the map and it wont break combat, so you still can't loot, right? Well....actually you can now go down to the bandit camp and loot the water. The water jug will still be there (even though you killed the guy before he was supposed to bring it across the river). When that happens, it starts the scripted event, and you get ambushed. When you kill those two bandits, it breaks combat! Now you can loot them, loot the beer and pistol, loot the dead guy in the lower right of the map, kill the 3 bandits between you and the camp, loot all the caravan people you killed (i think its like 20 copper each corpse!). However, you have to sneak to loot them if they died near the wagon, otherwise the caravan leader will see you and attack you (even though he's been maimed by the barbarians...he'll miraculously chase after you and kill you...and you can't attack him back). After looting, you can then sneak around the bandit leader who is now in the camp (taking credit for your kills!) so that you can loot Calisca (http://i.imgur.com/uoP00Qu.jpg). After that, there is a good place in the top right of the camp that you can get the bandits to line up single file so that you can kill them all. Then the beowic comes, and you're off!
I hadn't seen this posted before, so let me know if it's old info.