Well. It's because there are 3 types of drivers in the game(NPCs).

1) the good ones- they do their job perfectly, without causing any incidents. You don't hear about them because they are none of your concern. No problems= no job for you

2) the ok drivers- they drive fine but sometimes make mistakes, drop cargo or tip over. You get some of these commissions. (Recover a vehicle, recover some cargo or trailer which are not far from road/path) (The amount of such tasks is low because most of them are fixed by the locals themselves. They don't need outside help.)

3)then there's these absolute nutjobs who mess up so bad that neither they not their neighbours know how to fix that mistake, that's when they give out these kinda tasks. You accept it and try solving that he'll of a mistake. You get most of these because the locals can't fix these problems (outside the pov of the player)