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It's handled automatically, if you have an army in enemy territory it will loot, but i think the time it takes is variable. You can just wait with a small army until the place catches fire, then go to the next province. I don't know if army size or composition affects the time it takes to loot, however.
 
You cannot loot a city. And, unfortunately, fortresses are not reducable...
 
i'm not sure what you mean webbrave, but nearly every military action i've undergone has lead to looting; ie. those flames in a province which reduce production. Of course, you don't get any money or anything, it's in the soldiers pockets. And as far as reducing a fortress goes the manual says you can with an assault, but I don't recall that happening in any of my games either...
 
The thing with looting is that your enemy loses income for the province for one year. I agree it would be fun (and realistic I guess) if you got some money if looting a province, but it probably has something to do with game balance that you can't.
 
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And as far as reducing a fortress goes the manual says you can with an assault, but I don't recall that happening in any of my games either...

It happens once in a while during wars or rebellions. Not very often though.
 
That would be stupid because , If it were on Auto-Loot. I woudnt like my men looting a province before i annexed it(duh)~:)

Plz dont bombard Paradox with silly Looting Requests for the patch :)