My second attempt, pretty proud of it actually. Learned a lot after the first, which were on but not seated in the ear come morning. He yelped when he hit the ear on something or bent the ear, but I think that was more about the shock of something new happening to his head, rather than true pain. With his ears up, he looks like I have a doberman, not just a widdle baby.
He's been upgraded to a larger, wire crate, which he seems to settle in faster; or maybe he's just acclimitizing.