If I correctly recall, DR "knew of" the Wetterlings, although not well enough to know the Wetterling children or their ages. You're correct in that anyone hiding may have overheard their conversation, but why would DR know for certain they were returning. Maybe they were riding to meet a parent down the road, which my kids have done. Bike trips are not always two ways.
DR has a unique very low voice. It would seem the boys would have recognized DR's voice, his stature, his height. The picture profile, too, is of a man who would have been much older, heavier than DR.
I've looked at maps from the time period of the abduction -- DR's property is at the end of a road, the only thing on the other side of his property was Tom Thumb's (where they rented the movie).
To me, it seems strange to think that a man was just hanging around DR's place, waiting in hiding for someone to "happen" by. Whomever did this has given us clues of a degree of premeditation (perhaps minutes, perhaps days, weeks, months or years) - but premeditation nonetheless.
Someone was in the bushes... wearing a nylon mask, and carrying a GUN. That speaks to premeditation!
So to me, this had to have gone one of three ways (though I'm open to more theories if you have one to propose).
-> DR was alone at the farm, and heard the kids coming, ran in to the house or his car, got nylon and gun and hid in wait to abduct a boy on his return. If this was the case, he may not have been certain they WOULD return, but hoped for it, and may have figured that if they didn't return, then that would end his plan.
-> Perhaps DR had a friend over that night? PErhaps someone dropped by to visit him unannounced? (But if no car was there, then WHO? Would have to be very local!). Maybe DR knew the friend was over, maybe he never did know someone dropped in on him that night -- but maybe a person visiting in this fashion is responsible? Could be someone DR knew well, or only in passing -- someone stopping by to borrow something, to drop off something... whatever the reason. To me, if the perp had a mask and gun, I can't help but wonder about whether he had any drug deals going on with DR? Perhaps his original intent was to rob the farm house (the parents were away, did anyone know DR would still be home?).
-> DR's brother lives on the property as well, in a little house just before the farm. Not sure if he did at the time or if this happened later -- but perhaps someone was there to visit HIM that night? Or his family (if he had one back then?). Where was the brother at the time anyhow?? Just wondering.