My son knows how to hold a sippy cup, but hates to do it and has always preferred a bottle. Everyone around me was very adamant about giving up the bottle at 1, and I felt a lot of pressure! but my doctor told me it really isn't a big deal. Plus he drinks a lot more from his bottle then he does a sippy cup and I think it's helped him grow quite a bit. At my sons 18 month appointment the doctor said to start trying to use sippy cups more and at two he should probably be off of the bottle. I watch my sister in law struggle and fight with her 15 month old and refuse him bottles. There were days that I would try to make him just use a sippy cup and by the end of the day we were both so frustrated that in my mind it just wasn't worth it. I was starting to get really worried that he was never going to give up the bottle. But in the last month or so, I've started telling him, "okay you can have your bottle, but when you turn two, the bottles will be all gone." Now he tells me
"turn 2, no more bottles" and he's actually started doing really well with sippy cups and not fighting for the bottle so much. I'm really thinking (hoping, praying) that this is going to be an easy transition. And I'm glad that we didn't have to make a big fight out of it.
And as far as switching over to milk. I did a four week transition. The first week I would fill a quarter of his bottle with milk and the rest with breast milk/formula, the next week it was half milk, then 3/4 milk and then on the fourth week we were full on milk. He didn't seem to have any issues with it.