gypsy has always slept outside, i don't see the problem as long as they have plenty of shelter and a comfy bed etc, like said above gypsy had the option, but always preferred to
sleep outside, so thats where she stayed, much more to do overnight out their!
if your pup has never slept outside, i wouldn't just dump him out and leave him for the night, i would do it gradually.
"He is your friend, your partner, your defender, your dog. You are his life, his love, his leader. He will be yours, faithful and true, to the last beat of his heart. You owe it to him to be worthy of such devotion" Author Unknown