If you use the crate alot of the time, and keep it positive, he should go in quite willingly even for 'punishment.' Maybe you could cover some of it with a towel or something when his in 'trouble' to indicate the difference, and be sure to ignore him.
As you know, Sheba our gsd sleeps in the bathroom, on the worlds biggest dog bed. When we had her last winter, if she was just going in to be secure (ie away from the cats, or people, or we were going out) she had the light on, lots of fuss when she sat on her bed and occasionally a biscuit (but not every time - in case we forgot or took her up in a hurry, we didnt want her to expect it).
If she is 'in trouble' She is told once 'basket' and goes up with us, she gets no more verbal attention and we leave the light off. Shes only left for 5 or 10 minutes, but learned surprisingly quickly (for a rescued, previously abused dog) when she's being ignored, and when she's just going on her basket for a kip!
Henry is still learning the boundaries, so be consistant! Good to hear you're feeling positive though...