What happens is at a certain point we have to unload the part of the map the car is on, which means its headlights don’t cast light any more. It’s possible that if we keep making the game faster (which we have been doing over time), we’ll be able to enlarge the map area, but I’m not optomistic that we’ll ever make it large enough to fix this particular bug. The reason it’s so visible with car headlights is that they are the most powerful lights in the game.
Headlights are currently defined to always point forward, it’s possible to define them to point off at an arbitrary angle, and that’s a feature we’ll take a look at.