H.C.
I was wondering why you want to wean him from the bottle. I did some research for my older child who had a huge appetite but also screamed for milk. I don't remember where and what I read but I remember that my general conclusion was that children need milk till about 2 years old, so I let her have it. Her younger brother is now 16 months old also gets milk 3x per day, 5oz diluted with 2oz water. He doesn't scream for it, but he really loves the warm milk and the cuddle time, though he will also hold the bottle and drink it himself. I think waking in the morning can be a difficult transition time for them and milk is very soothing.
I buy raw goat milk direct from a farm so they are getting milk that is untreated and unpasteurised. Milk in this form is full of all the beneficial bacteria that get killed in the pasteruisation process so I feel that I am also giving him a really good high quality source of nutrition. It also enables me to give him vitamins and fish oil mixed in which he won't drink in water or juice.
I have never felt the need to transition the milk to sippy cups. They are hard to clean and he gets bored trying to suck it out - its hard work! so the milk often goes to waste when I find it under the coach 2 days later!!
I am not sure if you are trying to wean him off bottles, off milk or both. But I would go to a book store and browse the books on toddler nutrition and look on line to decide for yourself whether you think he needs milk still or not. Personally I have found that if they are drinking milk, a bottle makes sense. But you'll figure it out for you and your little one.