Yes, me too. At higher speeds wind noise is more noticeable especially from the front window pillars. I think it's because the inherit design of the car. I don't think more weather strips would help, but if it works for you that's good. I never drove a jeep so I wonder if they experience the same.
Never had that happen to me in a while, but I think it has to do with the pump itself, and it was probably random. If it does it most of the time with different pumps, then maybe there is an issue with your fuel port?
I had problems with the seats only on long drives 3+ hours. I got this seat cushion. I know they're pricey, but it has worked out for me, and there's discount codes on the internet.
https://thecushionlab.com/products/pressure-relief-car-seat-cushion
If you are in Southern California, I recommend Norm Reeves Ford. My experience was transparent and they did not add any unnecessary items on my order. What I reserved is what I got and that's it.