If the Impala didn’t cross over with them like it did in “Scoobynatural,” they would have to improvise weapons with whatever the Flintstones and Co. have on hand.
They’d have a hard time getting their hands on iron, let alone shotguns and holy oil.
Probably, and he’d probably get the same results as he did with Daphne.
The Winchester boys are no strangers to traveling back in time, but being sent back to a prehistoric time that has dinosaurs coexisting with people in animated glory?