Great post but one point, Whole foods sells 1/2 gallons for $6! I don't drink much milk but would gladly pay a premium for high quality, local, organic milk.
Please explain what "premium" milk is. Milk is a commodity. All milk has a code on the bottle that indicates which farm produced it. If you compare codes you'll often find the cheaper store brands are the same thing as the more expensive brands.
In New England Organic Valley is as good as it gets for store milk,
The dairy I worked at does sell high quality local raw milk; they have a pasteurizer to produce cheese, but they can't use the same one to produce pasteurized milk.
Additionally, the cows usually produce an excess volume of milk, which is sold so it doesn't go to waste: it's important to remember that even if the milk is sold for, say, $6 at Whole Foods, not all of the markup goes to the farmer.