Though I gather the immediate concern has passed, I have made some tweaks to looting that should make it much harder for a tiny number of defenders to prevent looting.
I would also like to clarify that when you get the message "X has attempted to loot but defending forces prevented the attempt," if the number of defending forces is small (especially when compared to both region population and number of troops of your realm there), this was your attempt failing a check, not an absolute block.
Try again, and you might be able to loot; other people might, too. Larger units will have an easier time looting against smaller defenders.