Shadow rendering on terrain in Orbiter...well, it sucks. It's pretty glitchy because all it can do is try to project the profile of the car as a 2D plane oriented to the local normal. The suspension animations of the car are similarly hamstrung because they are based on the orientation of the touchdown points to infer strut displacements.
It's not particularly easy to model the effect of caster on the steering, and as you say caster doesn't always work to resume straight travel unless you are on a more or less level road. Trying to manage the steering with a control definition would turn the wheel too quickly, and the sudden change of angle would cause skid when it normally wouldn't. Slowing that down with a delay made the steering very sluggish. Making incremental changes to the steering angle seems to work nicely.