Cannot tell from your pictures, however, every car I have ever worked on has the inner vapor barrier sealed to the actual door with some sort of sealer, sometimes single use sealer.
Here is what you must understand, water will get past the gaskets and into the door, this is "normal". The water will drip down in the door and will also stick to/run along the wiring, the door frame and window lift mechanism.
I have never had a door apart on my GMC, but my guess is the vapor barrier should be sealed to keep water from leaking between the vapor barrier and insider door skin. The Bose speaker may be sealed or have a gasket that seals in the opening as well.
If it was my truck, I would at least pop the drivers door panel at the bottom and peak up around the vapor barrier and speaker to see what it anything is sealed on this side.
Maybe the door was replaced on your truck, maybe the guy on the assembly line forgot to seal the vapor barrier and/or speaker?
Again, I have never seen any car or truck that the vapor barrier was not sealed in some way to the inner door skin.