I want to reinforce the point made by
@wittaj that the line likely needs to be even taller/higher/closer to the street than you drew in your second iteration. I encourage you to you look at an image of someone (even yourself) simply standing on your sidewalk, I think it will be obvious why you need the lines (or intrusion box) to be higher, even including a part of the street close to the curb. During daylight hours, the tires of a vehicle will be at least some distance into the street, but I acknowledge the potential problem with headlights at night. If someone is walking on the sidewalk, I suspect your current lines would barely cover the legs, and I'm just guessing that the person's head would overlap the street itself.