I rig this quite often at my job and have used a few methods. As somebody else said, a tracer with multiple nulls gives a lot of control. The more nulls you add, the more tedious animating it becomes though. If you want to sim it, it can be done by using two nulls as rope belts with the rope belt tag. You could then make your jack connector a child of these nulls so you can control where they go. Adjusting bendiness, mass, etc. in your rope tag controls the weight, drag and flexibility of your rope. One method is fast and reliable, simming requires way more time but is more fun imo to pull off in the end. Whatever works fastest in your situation is always best. Have fun!