Yeah, I'll probably be introducing whole milk pretty soon. Not completely, I will keep giving Morgan as much breastmilk as I can for as long as I can, but I'll start giving her some milk in between nursings. With Mackenzie I was giving her milk instead of a nursing before bed at around 10 months but that was because my milk supply dropped big time from being pregnant.
Anyway, in the US the guidelines for milk are to wait until 12 months. In Canada, it's between 9-12 months. I think the most important thing is that you start really slowly. Give an ounce or two and then gradually increase the amount you give him to make sure that his digestive system is handling it okay.
As far as the cup goes, I don't see any point in rushing to a cup. There's nothing wrong with a bottle, just don't let him fall asleep with it in his mouth. You want to be able to brush his teeth after he's done and before he goes to sleep. Mackenzie drank milk from a bottle until this past summer because we don't have a dishwasher and it was almost impossible for me to really get the milk out of those sippy cup things. She drank her water and juice from sippy cups, but until I found a better sippy cup (the playtex twist & lock...they're awesome!) it was milk in a bottle. My dentist didn't have a problem with it either.