I hadn’t really thought that far ahead! I bet the Winchesters (any set, if we consider the @brothersapart multiverse) would find this just as crazy as Bowman and Jacob do. Jacob would have even more mother henning to worry about while he’s so little, regardless of how big the Winchesters are!
Inspiration can come up and bite us at the most random times, so I wouldn’t say it’s impossible.
How I imagine Dean would react to a tol Bowman: