I've always wondered if the first car DR saw pulled in around the time Jacob and his father came home from hockey practice. I think that would definitely reinforce the belief that Jacob was stalked, and possibly even followed from the hockey rink. Obviously, DJH is a stalker based on the videos found and the police report of him following paperboys. Maybe DJH (or whoever took Jacob) saw a dead-end sign on the street when he was following the Wetterlings, so he turned around?
What time did Jacob and Jerry come home, and what time did DR see the first car pull around? The only problem I see with that is there being two different cars, and the distance between Paynesville and St. Joseph. Could DJH have pulled around, went home to Paynesville to switch cars, then come back? That may discount the possible sighting by the couple at Tom Thumb earlier in the evening. Maybe this was a crime committed with multiple perps (DJH's brother, Duane Hart), as some have suggested, and the tan Buick was close by (Tom Thumb?) with the other perp.