Wilson looks so withdrawn in his crate! he's probably pondering ways of escape! I think it's a good idea to let him roam as long as that doggy door is sealed closed so he doesn't go outside. Just check and re-check his surroundings to make sure it's a "Wilson-proof" and "Wilson-friendly" environment so he doesn't get himself into any trouble.
My goodness, is that Emma next to Wilson?!! she's such a big girl now!!