J.J.
Yes, typically you should wait until 12 months to feed whole cow's milk. Use formula or breastmilk until then unless your pedi specifically says otherwise.
As for the cup, my son also had a hard time transitioning. We started putting a little juice/water mixture in the cup. Because he really wanted the juice, he tried very hard to learn to use the cup. Milk just wasn't enough motivation for him! That taught him how to use it. Once we felt that he was physically able to drink from the cup, we went cold turkey to putting milk in it and no more bottles. Since we knew he could use it, we knew that he would drink if he was thirsty enough. It made me nervous for a day or two, but this is what our pedi told us. Sure enough, he adjusted fast and never asked for the bottle again. Truth be told, we didn't push the cup soon enough, which may be your problem too. We didn't try very hard until he turned 12 months. It took about a month for him to totally take to the cup. You may also want to try different brands. The favorite in my house and among most of my friends is the Playtex cups. Kids seem to like them and they don't leak!