First things first, he had to get a look at that body and see what was up... which meant using some of their money to bribe his way in at the morgue. Definitely right up their alley after he got a glimpse of the guy. Eyes didn't look like that after a stroke or whatever they were claiming.

Then it was talking to the family and seeing what the hell was up on their side of the story.

Eventually though, he made it back to the motel and made sure the trunk was open by seven... didn't want Dean trapped in there. Had to be crappy enough being in there all day, but to wake up stuck? Yeah, not something he was going to put Dean through.