That scenario is completely missing the point. Bob has to drive because of the lack of good public transportation and the fact that he can't afford a house near his work. Not to mention if he can't afford a car with insurance it's because his job simply doesn't pay enough.
It's much more likely that external factors put him in that situation, rather than himself. Yet you propose we should punish him personally and paint only Alice as a victim. That's naive. Both are victims.
These are systemic problems and trying to solve them with individual punishments is only going to hurt individuals while not fixing the underlying issues that really matter.
I'm fully aware Bob is the victim. That's why I'm saying the solution is to make it so Bob didn't get in a car. He is a victim of car dependency. Subsidizing insurance to make sure Bob could always afford it isn't solving that. Ensuring he can always afford insurance just furthers his victimhood.
But the only question that really matters in the end is: is that profitable?
If we really cared about safety many people would not be allowed to drive in the first place. Tests would be much more strict and rightly so. But it's way more profitable to let those people spend money on cars (and eventually kill people) than it is to provide good public transportation.
Especially with the auto industry, they have basically won the lobbying game. Most people can't even imagine a world where cars aren't in the center of it, so we keep moving the goalpost...
It's much more likely that external factors put him in that situation, rather than himself. Yet you propose we should punish him personally and paint only Alice as a victim. That's naive. Both are victims.
These are systemic problems and trying to solve them with individual punishments is only going to hurt individuals while not fixing the underlying issues that really matter.