I've had my truck as a daily driver for a year and a half now. And on four separate occasions I've tried starting it and it just makes a terrible cranking slash grinding sound. But if I try and start it again it'll start up fine. Any idea on why this keeps happening?

 

Sounds like a ring gear that's missing some teeth

 

Or maybe the starter is hanging up and not going all the way out and just barely hitting?

 

I would take a good look at the ring gear and starter for chewed up teeth.

 

If you the truck doesn't move in between startup attempts, then it might be the bendex gear in the starter. My truck does the same thing, but it happens so infrequently that I'm not concerned with fixing it. Sometimes, I have to put it in neutral to allow the truck to move just a hair, then try go again.