Oh yeah, he knew for sure. He didn't want to drive any further but it was his job and so he did it. But when the punk said "bit of this, bit of that" it was confirmed at that point someone in that car was gonna die. And assuming since the song said "Run" I don't think it was a warning to Ray.
Whenever an acquaintance asks too many questions I ask them if they're a cop. When they respond in the negative I say "Well you f*ckn sound like a cop".
If it's the handbook I'm thinking of it was actually written (supposedly) as fiction by a middle aged housewife, who accidentally wrote probably the best contract killing manual ever.
I think that guy Raphael killed her after the accident. She was his girlfriend when she first met Ray in that garage. He introduced her to Ray, then she started seeing Ray and I think Raphael got pist off about it and killed her after the crash, Ray had left in the camper, he also tried to kill Ray at that farm, but Ray got him first.