Can you take a quick picture of where your driver side drain plug is? I still have no idea where it is - perhaps the skid plate is covering it

I found one leak on the top of the tailgate - where the radio wires go inside the cab that grommet was brittle and lifted up. This exposed a pretty big hole to the interior that ran inside the paneling down to the floor. I'll post some pictures soon.

 

It's not very easy to get a picture that shows it very well - with the low ground clearance I can't get far enough out to show the entire area of the skid plate that has the grommet. It's NOT the gray round plastic pieces that look like they snap in/out. It's a flat round rubber black piece about the size of a quarter that will pull right out when you get under the edge of it - the water will gush out. The driver side plug is more to the inside of the vehicle than the passenger side plug was. It's hard to see because its flat to the plate and on the innermost edge of it. If you still can't locate it LMK and I can jack the Durango up and get a better picture.

 

Driver side grommet is indeed under the skid plate. There is only one and it is smaller in size as compared to the two on the passenger side.