Wilf,
1- Strategy is the use of force in the service of a Nation/State Policy, which makes it a War, which should have an End. When force is used by a Private Person or Private Organization it is a crime. Something that Police Officers are trained to deal with from day one, and we also understand deescalation as opposed to escalation,Armies are not good at those things. The Strategic Framework is Motive,Methods and Opportunities. The main motives are Greed,Power and Revenge. Because of the human condition I see no end to be achieved but you can establish a process to suppress it (crime) to an acceptable level.

2-I am not sure about your money question. Many LE organizations (not just DEA) seize assets both local and foreign on a regular basis. Criminal organizations are like insurgencies in that they need people,guns,and money to exist. When you focus on those three, mostly people and money you can suppress it effectively.

3-Pablo may or may not have been dumb but he acted like most criminals and rich people he became drunk with power and felt he was above the law. Which led to his downfall.

4-I am not surprised you see a CvC parallel with attacking Pablo's supply lines the more I read CvC again and again the more I am convinced he would have made a better Cop then General. The first targets against Pablo were his Lawyers and Bankers an adaption of what I call the Shakespeare Method of crime control.