H.G.
I'll tell you what worked wonders for my son.. Walmart Nuby cups. They are still "bottle-like" (very soft spout), but he can hold the handles and drink completely by himself. I still have to hold him though so he tips it back enough. It only took me one day to get him off the actual bottle. I haven't really tried getting him to drink it out of other sippy cups though, but he's only 10 months old so I'm not going to rush it... Also, have you thought about maybe warming up the milk?