I would suggest the casein then after your workout. This way you don't have to stay awake to burn through the extra intake. Does this help?

There is no way I would be staying up just to let the milk metabolize. And unless your are drinking tons of the stuff at once it's only a couple hundred calories.

If it's your recovery drink then your body would QUICKLY absorb 8oz. of Chocolate milk I would think. Make sure you aren't taking the junk with High Fructose Corn Syrup in it. I know Nestle Quick makes it without it in it's powder. Don't know about the pre-made stuff. After your workout your body is starving for Carbs and Protein. I think you can drink it, take a shower, relax for about 20-30 minutes and then go to bed if you wanted. By the time you did that the total time would be about an hour anyway. I don't think you'd workout, drink your chocolate milk and go directly to bed all sweaty and panting heavy would you? LOL. 1 cup of 1% milk and 2 teaspoons of Quick= 160 calories.

recovery before sleep can consist 30-70 grams of casene, with some fibers end essentialy fatty acids is the best choice

Avoid shugars 3 hours before sleep, it raises insuline wich inhibit GH output, as you know GH output is at sleeping time biggest so dont do this

I just did that last night. Chocolate Milk (with whey) after workout sat for about 10 mins, showered then went to bed. Finished the workout at like 12:15am. Went to sleep at like 1am. I know thats really late but it shouldn't be a problem.

The biggest problem with late night workouts is not getting enough sleep. The body needs that full 8 hours or close to it. I used to work out later at night and would have the problem of not getting enough rest.