i'm not going to be much help, our dd had gastro when she was 11 months and wouldn't drink her bottles so she gave them up cold turkey (she was having 2) and she just loved her cup... first we used an avent bottle with handles and these drinking spouts which you can put in (so then it was still her bottle but more like a cup) this worked well. then we used playtex cups they were the best!!
good luck hope someone has better advice for you, it was realitivly easy for us but that's cause she was sick!!