A lot depends on how much you drink. Every glass of skim milk has 80 - 90 calories, this can add up fast if you drink milk like my husband and aunt do (a gallon in a day or two). This is why I laughed when I heard that Dr. Kavourkian had gone on a milk and juice fast as a "hunger strike." It's not much of a hunger strike, in my opinion, if you could maintain your weight on it.
Many people interpret "milk may help you lose weight," as "the more I drink, the more I'll lose." If that where true, infants of all mammal species would starve to death before they were able to eat solid food (or if we're only talking cow's milk, at least baby calves would).
Any beverage with calories has to be considered a food, not only a beverage, and so you have to treat it that way. You have to also know that the body's hunger/fullness mechanism doesn't always work the same for liquids as solids. Solids tend to satisfy you for fewer calories, which is why so often you hear people suggesting you limit or avoid drinking your calories.
If I haven't completely confused you yet, I think it's safe to say there is no black and white answer here. You very well may have to watch the scale and experiement.
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