the stupid thing with people being all obsessed about the idea of cas choosing the winchesters over heaven, though, is that:
“Imagine it, Castiel, for you to come and go as you please. Be part of your family, your true family, again.”
the entire point is cas not having to chose in the first place. he can be with the winchesters and on earth when he wants. he can be in heaven and with the angels when he wants. he can have both.
but, y’know god fucking forbid cas has happiness and joy outside of
dean the winchesters.