My first thought on the stroller it that does not appear to be stowed for traveling? Seems to me that for the best results one should stow it and place it in a travel bag. That said, that toss is pretty hap hazard. As for the bags, my guess is the ramp workers have learned that unless the bags have some inertia they do not slide down the chutes all the time. Which some has to climb up and retrieve them.
The lesson should be do not gate check your bags and pack your bags like they going to be treated like this: