Door and truck stripping

From the pictures it does not appear that there is a problem with the window gasket. It is not uncommon to have a gap show in this area between the trim and the a-pillar. Water can always easily flow under the chrome trim when done properly. You problem is more likely in the bottom corner of the window, where there may be a rust hole allowing water to enter the car and drip exactly where it is on your floor.

Grant

Dito

Calking would be a waste of time. The only way to stop a rust hole leak at windshield and rear window is to remove glass, and weld in a patch... If in fact that is were water is coming in.

I think you need to do a little more detective work first to better pin point the problem.