Hi Leah I have a 15 month old little boy that we took off the bottle at 12-13 months. We tried for about 3 weeks until it took. I bought every kind of sippy cup they sell. The one that seemed to work was the Nuby cup they are cheep and they have a soft nipple like the bottle. He will drink out of any cup during the day and at day care but he has to have the Nuby at night (it may be as bad but it's still not the bottle). I also have the same problem he still gets up at least once for a cup and it must be milk. I have tried water but that's a no go, I am very particular about teeth so he brushes his teeth twice or more a day. I am like you I can not stand to hear him cry for hours upon end. I may be criticized like you have been in some of these post. I work 50+ hours a week so they can just leave us alone. Good luck and you should really try the cup and resort back to the bottle in the middle of the night just if she does not want to take the cup and it will stick.
Shannon