I think the key is the application. The 250 psf is a uniform traffic surcharge that is used to represent traffic as it flows along the top of the wall and the superposition of thier wheel loads. In analysis, because it is a uniform surcharge, the surcharge times the appropriate K value is applied over the entire height of the wall.
My understanding is that it is not meant to represent a truck parked for long periods of time at the top of a wall. Such a truck would cause a high point load, but the load would be distributed with depth using a Bousineque (sp?) or 2:1 approximation. Therefore the top of the wall may experience localized higer stresses, but overall less than the 250 psf.
How close to the wall will the trucks travel? A conservative approach would be to determine the loading on the wall due to a parked design vehicle or the 250 psf loading, and design for the highest loads. My assumption, having not done any calculations, is that if you design for the moment and shear of the 250 psf surcharge load (plus the appropriate soil loading, of course), you likely will be designing for a higher bending moment than the static truck loads.