First of all, kudos to your husband for enforcing the training "words" despite being half asleep...AND...being the one to get up and take him out. That is rare in my experience, and from what I've heard, I'm not the only woman to say that, so well done, both of you!
It's also wonderful to hear that already Rollie finds his crate to be his safe place. As you said, it is understandable that he doesn't enjoy suddenly finding himself alone. That is perfectly normal. Putting himself to bed, in the crate, for a nap is also a terrific sign.
Enjoy your weekend with Rollie!